Where are you risk-blind?

Do you ever look back at a thing you did/made/said and think: cripes, that was risky? I’ve noticed that many of the leaders I work with don’t. (Or not regularly.) Not because they’re risk-averse, but because risk is just part of how they roll.

They might not dwell on it, but the big stuff is hard to miss: experiments with cross-industry collaborations[1], founding start-ups, even delivering life saving vaccines in lockdown.[2]

But not all risk is so well signalled. Not all of it is so swiftly noticed. And not all risks are ones you actually choose.

Notice what you choose

Noticing is the most versatile and least glitzy of superpowers. It’s genuinely hard to make it sound exciting. But paying attention to the risks you’re taking, or asking your team to take, can be revelatory.

It’s not just about what and how much, either. Notice which risks are chosen, and which aren’t. Notice the balance between them. That balance matters. It has an impact not just on how much risk you take, but how you take risks, and which ones, and the degree of effort you invest. More than anything, it’s hard to take more chosen risks if your energy is tied up in all the unchosen ones.

🧐 Get curious about your unchosen risks

Some unchosen risks are a response to uncertainties beyond your control. Others might be consciously chosen – just not by you. Either way, get curious about where you’re experiencing unchosen risks in your work, home, health, family, community, environment, or elsewhere. Look beyond the obvious, too. What’s slipping under your radar? What are you downplaying even though it’s consuming significant energy?

Get curious too about where you can exercise choice within the unchosen. Which unchosen risks might you be able to mitigate? How might you influence their progress or outcomes? And which might actually give you some unexpected space to play. Sometimes what you don’t choose can be just what you need.

🧐 Get curious about your chosen risks

Intentional risk can be thrilling. (Provided you remember that not knowing the outcome is what actually makes it a risk.[3]) So get curious about where you’re choosing to take risks. What are your big gambles? Where are you running test—learn—adapt style experiments for small, swift and persistent progress?[4] Which bits of you could withstand a bit more risk? And which bits need a lie down and some time out?

Get curious too about what happens as a result of these risks. What are you noticing, what are you finding out? How it is shaping and creating who you are – and who you might become?

🧐 Get curious about your team’s risk balance

What feels risky to you might not to your team. But also: vice versa. So get curious, about the team as a whole, and as individuals. What is the team’s balance of chosen versus unchosen risk? Who is currently drained by unchosen risk that’s nothing to do with work? How might you reduce or redistribute some of their chosen risks?

Get curious about where they lack risk, chosen or otherwise.[5] Which risks are the team aching to take? Who is desperately craving more chosen risk, or risks beyond your team? Where are you unwittingly heaping more unchosen risk on your team, or reducing their space for chosen risk? And who is choosing risks, and for whom?

Run a risk audit (not that sort)

You’ll find chosen and unchosen risks almost everywhere in response to this VUCA, post-pandemic, gen AI world. And since merely being human comes with its own mess, delight and tragedy, there’ll be plenty of both in the analogue world, too.

So run a current risk audit.[6] Which apply to you, which to your team? Which are chosen, or not, and by whom? Where else might you look? Getting curious might not change the choices available to you right now, but it might help you decide between them with greater clarity.

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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FOOTNOTES

1 Music streaming and healthcare, in case you wondered. Bewildering but also, it transpired, a stroke of genius.

2 An unexpected delight amidst the awfulness of the pandemic was being able not only to thank them, but to pass on the thanks of the nurse who gave me my first jab.

3 If you could guarantee that it wouldn’t be a risk. Which is surely obvious, and yet so frequently forgotten. Weird. 🤷‍♀️

4 This kind of experimenting enables you to take small risks and learn fast so that you de-risk the big risk. Intriguingly, it’s not uncommon for teams to launch straight into the massively risky big risk because the much small risk of experimenting feels… too risky. 🙃

5 Unchosen risk is part of working life (as well as life life), so protecting your team from it isn’t terribly helpful. Luckily, there’s usually plenty to go round.

6 A short, regular audit that’s current is often more useful than the big the review that’s out of date by the time it’s finished. Besides, while it’s tempting skip ahead to the sunlit future uplands, but actually, what you’re experiencing now will influence what happens next.

What have you lost?

Hello, lovely to get curious with you again. If you’re new here, welcome! If you’re a long stay subscriber, thanks for sticking around! Let’s dive in.

A conversation with a stranger caused me to notice some things I’ve lost of late. A notebook habit, persistent risk-taking¹, spotting wildflowers in the street. These losses aren’t catastrophic. But they do make me feel somehow less… me.

It’s alarmingly easy to find that bits of yourself have gone astray. Not just good habits², but who you are (or thought you were) solo or together. Does that matter? And if you want it back, where on earth should you look?

What have you shoved out of sight?

Embarrassing admission: when I started Chirp I invisibilised the artist bit of my career.³ I didn’t think anyone would get it, much less value it.⁴ So my artist self stayed out of sight. (I even ditched the edgy fringe.⁵) It took me ages to notice that my niche blend of career was actually the point. And even longer to own it.⁶

It happens in teams, too. In an identity workshop I ran a while ago, a sidebar chat unearthed a stash of hidden gifts – from deep visual literacy to an intricate knowledge of gaming.⁷ Was this stuff core? No. Had dismissing it hampered their success? No. But it had prevented the rest of the team from leveraging a pile of (bonus!) skills, knowledge and experience.

We all shove aspects of ourselves out of sight, for all sorts of reasons.⁸ But what are you truly willing to lose? What might be valuable now even if it wasn’t then? What do you want to find again? This is a timely moment to look: wittingly or not, we are building the future. So get curious:

What have you downplayed?
Which aspects of yourself do you rebuff?
What are you unwilling to lose?
Which unheralded gifts might your team reveal?
Who couldn’t you be before but might be now?⁹

What have you inadvertently mislaid?

Stuff gets lost by accident, too. Another team I worked with had embraced asynchronicity so heartily they’d lost the knack of picking up the phone.¹⁰ They still had team meetings, but their ad hoc “10 minutes to figure out” or “quick take on” had disappeared. And losing those quick, on the fly connections had also slowed them down. But it didn’t require wholesale change. Just noticing what was mislaid, and choosing, judiciously, to put it back.

Sometimes it’s personal. A rueful I used to be… is something I quite often hear from leaders. And on the surface it’s fine – they’re over it. But it niggles because what’s missing feels somehow fundamental to they are.¹¹ Happily, a lot of being is actually doing: I do therefore I am. It needn’t be big, or constant, or superb. Doing is still becoming. So again, get curious:

Who do you miss being?
What did you do that made you be?
What might be its easiest, most appealing iteration?
What are you willing to trade in exchange for doing it?
Who are you without it? And why does that matter?

Audit your lost and found

Many of us have lost things beyond the plain heartbreaking over the last few years. Some we’re deeply aware of; others rest below the surface. But we can choose to audit that lost and found – for ourselves, our teams, even our organisations. So have a good rummage. Notice what’s missing. Where might you find it? Do you still want it? (You might not.¹²) Notice what’s turned up. Is it useful? Is it in the way? Perhaps you’ll find what you were looking for elsewhere. Perhaps it’ll look a bit different. And hey, maybe it was never quite lost in the first place.

See you next time! 👋

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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FOOTNOTES

1 More on this next time.

2 BJ Fogg’s behavioural model is interesting on this, and why tiny shuffles might be the path to big strides. Thanks to Do Manifesto for the reminder, and the conversations that inspired this blog. (And that nice Nick Parker for giving me his ticket!)

3 To invisibilise: in common usage but as yet invisibilised in the dictionary, AFAIK (which isn’t).

4 Or… FIND IT ONLINE. 🤦

5 I still didn’t look corporate. Just unfringed.

6 Different times, innit? 🤷‍♀️ Plus it can take metaphorical balls of steel* to own who you are. In some contexts, just showing up is a radical act.
*I’m not fond of that phrase, but my feminist rendering is NSFW. 🙄 Which is particularly sad because it is also HILARIOUS.

7 Apparently it’s not just Pac-Man. 🤷‍♀️

8 FWIW, my thoughts on navigating the messiness of bringing your whole self to work.

9 Inspired by Ethan Mollick’s excellent question ‘what impossible thing can you do now’. Looking forward to reading his book – anyone else ordered and keen to discuss?

10 I think it’s an art: knowing when it’s the smart choice, having the confidence to ask, knowing how to use it efficiently.

11 My hunch is that these conversations are happening a bit more now because many of us have just enough distance from the pandemic to reflect on where we’ve landed. Who we were, and are. What we’ve gained, and lost. What we’re trying to find.

12 Like losing a fear of being found out, or sloughing off what isn’t yours – other people’s assumptions, say. Noticing this stuff can help you savour your success, own who you’ve become and choose where you go next: deliberately, and unencumbered.

Are you stuck in the effort swamp?

Ugh. My client’s response at mere mention of that task. 😣 But why such doom? Was it boring, or tricky, or scary? Nope.

And yet an unassuming item on the to-do list had become insurmountable – and thrown a brilliant leader into calamity. Not of the racing heart, bitter self-doubt variety. This was altogether more lackadaisical. My poor client hadn’t crashed, so much as gently roly polied into the effort swamp.

What is the effort swamp?

Take a look at your to-do list. Which item stubbornly resists removal? Or keeps falling off? Or spurs you into high performance procrastination? There’s a good chance it’s belly flopped into the swamp.

The effort swamp tends not to affect the big and dramatic, or even unutterably dull, so much as the squashy middle. Where the rewards seem simply too intangible, incremental or snoozily mañana.¹ And where boredom arises less from the Thing itself than the endless not-doing of it.

Stuff you can do, would benefit from doing, but also won’t die from not doing often thrives in the effort swamp. Which perhaps explains another of its intriguing features: the self-stymie. You don’t do it, so there’s no benefit, so you were right not to do it. QED. 🤷‍♀️ A glorious cart-before-the-horse call to inaction.²

A few IRL examples:³

• A client who hasn’t got round to reviving a valuable learning exchange because the admin might get onerous
  Even though they could cap the numbers, or crowdsource a solution (or… whisper it… discover there’s not that much demand)

• A mate who never quite has time to sort out their website because it doesn’t drive much traffic⁴
  Even though it doesn’t drive much traffic because it doesn’t work properly

• And me(a culpa)⁵: a product I haven’t finished because the sales might not recoup the faff
  Even though they definitely won’t if it never goes on sale 🙄

What with the not dying thing, the effort swamp is easy to dismiss. But being not bovvered is, annoyingly, quite a lot of bother. Thinking about whether to do the Thing is effort. Finding stuff to do instead is effort. Bashing yourself over the head for not making the effort is, yep, effort. It’s just not effort well spent. So what to do?

Ask impertinent questions 🤔

Does it actually matter?
What might happen if you just get on with it? Why is it more strategic not to bother? What might happen if you never do it?

Are you luxuriating in the swamp?
Which obstacles are real and which imagined? Where are you moved by a spirit of perversity? Where are you cosying up to being crap?⁶

Who might you become?
Who might you be if you climbed out of the swamp? Who might you be if you don’t? Which is scarier?

Fancy an expanded version of these Impertinent Questions? Download it here. Keen to get nosy every day? You might like my month of Impertinent Questions. (Fear not – you get weekends off.)

Budge the grudge

The effort swamp is often mired in a perception of drudgery – and real resentment. One day you’re mulling over the task; the next you begrudge everything it stands for. Like my mate who agreed to speak at an event, couldn’t decide what to speak about, and then told me all talks were boring, stupid and futile anyway. 😫⁷ Druge begets grudge in almost touching mutualism.

So get curious. Where might you find the fun and skip the swamp? Which bits are truly unavoidable? How might your ugh be another’s ooh?⁸ Even if the drudge (and grudge) doesn’t crumble under interrogation, at least you know what’s what. And that gives you a chance to make it less boring/tricksy/draining.⁹

Start anywhere, strategise en route

Leaders are frequently encouraged to set the course before they set off.¹⁰ And (provided you’re pivot-ready) that’s smart. But when you’re in the effort swamp? Not so much. Because you probably know the route and destination. You just can’t be arsed to go.

At which point, setting off from anywhere, in any direction, at least sets you in motion.¹¹ And offers a clearer view of what’s ahead. Yes, it might’ve been smarter to start elsewhere. And yes, you might have to change course. But that might’ve happened anyway. And at least you’re not still stranded at shore.

Know when to fold ‘em

Look around you. What’s changed since you stumbled into the effort swamp? Does the Thing still matter? Do you still care? What might you gain by ditching it altogether? And how will you feel: like a weight’s been lifted, or like you’ve dropped the ball?

Sure, sometimes you have to grit your teeth and crack on.¹² But there’s merit in knowing when to say feck it, I’m out.¹³ And to acknowledge that, if you haven’t done it yet, you’re just not going to. At least you’ll be making a choice. And freeing up all that effort for something you might want to do instead.

Goodness, you’ve read right to the end! If you’re new here, 👋 and many thanks for subscribing. And if you’re a long-standing (suffering?) reader, hearty cheers for sticking around. 🙌

If you’d like even more from me, there’s my month of Impertinent Questions, a 30-second read direct to your inbox. Actual real people have said nice things about it like ‘just so good’ and ‘I think it’s magical’ [*blushes with gratitude*]. There’s also my small back catalogue of blogs and now slightly old-ish podcast with still excellent guests. And if you’d like to chat curious coaching or leadership learning, just hit reply. And that’s it. PHEW! See you next time!

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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FOOTNOTES

1 A sort of Goldilocks gone wrong, where just right is just wrong.

2 Although the April 1907 edition of Popular Mechanics notes that “the very latest Paris novelty in the vehicle line is a four-wheeled surrey in which the cart is actually before the horse.” And (lolz) that “another feature which attracts attention is the driver, who is a woman.” (Also, just so you know, the first story on that page references suicide.)

3 To everyone who shared their effort swamps with me: thank you! To everyone else: don’t judge. I reckon we’ve all got ‘em lurking somewhere.

4 This came up So Many Times, with many a website/CV/profile update stuck in swampy sludge (including my own 😬).

5 This blog is nothing if not meta. Alarmingly, it might be nothing but meta. 😬

6 I’m all for purposeful crapness, as distinct from the feckless sort in which you give good sense the slip.

7 It was quite the diatribe – but, predictably, he was brilliant in the end! 🔥🙌😂

8 Their opportunity to gain skills/kudos/recognition, rather than yours to get rid at their expense – obvs.

9 Perhaps by deploying Second Brain, or being somewhere other than your desk, or playing it for laughs to boost your creativity (or just keep you awake).

10 Not least by me! 👋

11 It’s like steerageway, a sailing thing my mate Nick told me about: you can’t steer until you’re moving.

12 One Step Forward might help if so.

13 Or to quote our Ken: you gotta know when to hold ‘em, know when to fold ‘em. Apparently while performing a slow, polite striptease.

Are you an inadvertent completist?

The holidays are fast upon us. Books, sea and shaggy dogs lie almost within reach. But reader, I’ve stalled. And feel like I’m wading through porridge sans spurtle.

The diagnosis? Inadvertent completism. But hey, at least I'm in good company. Because however brilliant they are the rest of the time, most leaders succumb now and then.

But what is this inadvertent completism?

A kind of rubbish reverse alchemy, in which the more effort you make, the less value you create. 😫 And tragically, it can be contagious.

Here’s how it looked for a marvellous leader I coach. He’d just taken on a new team and was implementing a new vision and strategy. It was a massive undertaking, hugely exciting and he was rocking it.

BUT

Despite talent, experience and sheer drive, one solitary piece of work clung limpet-like to his slate. The more attention he gave it, the longer it lingered. The more he looked, the less he saw. The more clarity he attempted, the more convoluted it became.

The problem? In his laudable desire to offer something fulsome and complete, he’d inadvertently created a bloated, unwieldy palaver. And whereas ordinarily he’d use his fine judgement to:

Decide what matters, what doesn’t and which trade-offs to make
Choose when to pursue and when to pivot
Deliver excellence, not everything

Struck down with inadvertent completism, he’d:

Overshot enough in favour of comprehensive
Rethought, refined and revised as if stuck in an interminable game of Tetris¹
Generated extra work for everyone, as work begot work begot work – but infuriatingly, not value

Inadvertent completism, he lamented, is the unwanted gift that refuses to stop giving. You (and your team) continue to work harder, go deeper, do better – with inverse returns. Clarity of purpose crumbles under indistinct swathes of intention. Optimal value melts into valuing everything.² Confoundingly, more ends up as less.³ 😭

But why does this happen?

Inadvertent completism tends to descend at crunch points. During overload, for example, like my pre-holiday overwhelm. Or extreme flux, like when you try valiantly to craft clarity in an uncertain abyss.⁴ Or, perversely, when you do everything you can to hit the ground running, like my frustrated coachee.

And it’s not silliness: the leaders I work with are smart, strategic and familiar with brilliance.⁵ But almost everything has a flipside. So occasionally, in avoiding under-delivery, they lean into a metaphorical cross every t dot every i overcorrection. And in going above and beyond, end up deeper in the mire and further from the finish.

It’s no fun on the receiving end, either. Like when an otherwise wonderful exec I worked for requested just a bit more, and a line here, and perhaps a detail there on a treatment we were developing. The result was undeniably more complete. But it wasn’t better. And wasn’t commissioned anyway. 🙄

Yes, hindsight can over-simplify: there’s every chance it still would’ve bit the dust. But it might’ve been a smarter use of our time (and less infuriating) to deliver enough to fulfil the brief – and then crack on with something else.

But is there a cure?

Yes, of sorts. Get curious. Find out what works for you, and how you could adapt it for a better fit. You might, for example, give One Step Forward a whirl, or experiment with one of these.

🧐 Frame the negative

Rather than picking out what matters (usually everything), strip it back by framing the negative:

How isn’t that bit essential?
Where isn’t this thought relevant?
Why shouldn’t you address that, or that, or this?
What can’t you know?
What don’t you need to know?

Yes, there’s always nuance. And yes, it’s all probably important somewhere at some point. Just not all of it now.

🧐 Set creative constraints

An artist friend of mine often extols the beauty of boundaries when mentoring stuck colleagues. Because it might sound like (or be sold as) freedom, but delivering without parameters can be a nightmare.⁶ You often waste untold energy just wondering where to look. Her fave constraints?

Specify the scope
Specify the first, real audience (not future, potential audience)
Specify an imminent deadline for review with a specified person

Your parameters might change but, much like framing the negative, creative constraints can re-energise the process and give completism a firm kick.

🧐 Ask Impertinent Questions

Inadvertent completism won’t look the same in everyone. So get curious about when, how and where it manifests for you, and impacts on your team. The clearer the diagnosis, the faster the remedy.

When do you tend towards completism?
What are your completist triggers?
How might more doing produce less value?
Which of your expectations are unsustainable?
Where is there more solution than problem?

Plus a bonus: deploy Second Brain.⁷ It’s much easier to puncture inadvertent completism with a co-conspirator. Saying stuff out loud helps you spot where you’ve supersized the brief. Or where the brief is batshit. Plus: it’s much nicer to shed one’s excesses with companionable giggles than self-flagellation.

And to avoid inadvertent completism, that’s it! I’m off on holiday.⁸ 👋

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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FOOTNOTES

1 Which turns out to be actually possible, albeit in theory.

2 See also the “Everything Slide”. Awash with detail, utterly impenetrable, intriguingly common.

3 Incidentally, inadvertent completism isn’t quite the same as other personal tripwires. And since different ailments require different treatments, it’s worth checking you’re not actually suffering from high performance procrastination, perfectionism or luxuriation (stretching into the expanse for the sheer love of it).

4 On which: years ago I worked with a leader who’d inherited a restructure with another on the horizon and a potential merger. Completism was barely avoidable. One Step Forward helped her craft some clarity – but crikey, what an onslaught.

5 Which has its own issues.

6 Although marvellous for radical imagination, conjuring with impossibilities and escaping idiosyncratic shackles. Just less so when you have to produce something now.

7 Second Brain = conversational approach that helps you move forward. With a specifically selected Second Brain. A bit like coaching, a bit like mentoring, a bit like consulting. But also not quite. I meant to share a download but: inadvertent incompletism.

8 “Celebrate, holiday, celebrate.” Etc. 🥳

How do you show the love?

The other day a client asked me to define how I work with leaders.

“I show them the love.”

It’s true. And often why clients hire me. But it still feels bold to say it out loud.

Which is odd, because showing the love is a leadership superpower. One that’s powerfully enabling: it channels you to elevate everyone. And I love showing, feeling, and seeing others show the love. But it doesn’t get nearly the recognition or analysis it deserves.

Why is that? And why do I feel bold for owning it? Perhaps it feels safer to stick with Certified Leadership Credentials(TM). Or perhaps it’s another, related reason: showing the love is tricky to pin down. You know it when you feel it. But what does that mean? It is touchy-feely-yuck? (Let’s just get this out the way: no!) But also: wot?

Well, exactly. Which is why it’s only in recent years that I’ve fully embraced it.[1] And only now that I’m writing this.[2]

What is showing the love?

Showing the love isn’t something you do. It’s a feeling you communicate. But it’s hard to quantify a feeling. And even harder when it can be created differently by different people. But again: you know it when you feel it. Which is exactly what happened last week.

I was observing a workshop. My colleague was in the thick of it, delivering to a polite if wary crowd of senior execs. But as the session began to unfold I noticed their reticence give way to a kind of, well, exuberance:

Enthusiastic chipping in instead of waiting on (other) volunteers
Intense curiosity about where they aligned or diverged instead of just skimming the surface
Having an actual conversation instead of just saying answers[3]
Speaking honestly instead of keeping it safe

What was behind that shift? Right from the off, she showed them the love. She dialled into who she is: upbeat, irreverent, unafraid. She showed up with total clarity of intention: she wasn’t vague or hesitant. And, although showing the love isn’t without risk, she embraced that risk and leaned right in.

Let’s be clear: she also had great content, buckets of experience, and trusting sponsors. But the commitment from those leaders wasn’t just down to what she delivered. Or to buy-in from the big boss. It was a response to the feeling she created – by showing the love.

But how do you show the love?

Not necessarily like someone else. Which, again, makes it hard to quantify. Let’s dive into another example, this one with a very different vibe.

A mate of mine regularly tutors on a residential, application-only course. The tutors are experts, the attendees cock-a-hoop to be there, and unsurprisingly it’s all marvellous.[4] Except last time, the final exercise flipped his group from triumph to freak out. A week of excited thinking, talking, doing then:
S I L E N C E.

He could have ignored their discomfort. Or rescued them. Instead, he showed the love. What did that look like? Enabling them, with all of his compassion and acuity, to get curious about their discomfort. What was its texture? Where might it have come from? Where might it take them?

The love was there in his choice to lean right into who he is: perceptive, compassionate, kind. It was in his clarity of intention, and the feeling of safety he communicated.[5] It was there in his willingness to risk his own vulnerability. And because they felt the love, the group managed to swim with their discomfort and get home safely.

How and why they showed the love was different for my mate and my colleague. But I think they exercised similar muscles to help people feel it:

Leaning into who they are to create a personal connection even in a crowd[6]
Leading with clarity of intention instead of being vague or intermittent
Dialling themselves up to be a bit extra instead of doing extra
Meeting people where they are so they feel seen, not unsafe
Embracing the risk of showing the love, with no guarantee of the response[7]

What does it feel like?

Noticing how you feel the love can help you figure out how you show it. So here’s an example from a recipient of the love – me.

I was leading a precarious project. Think: widespread reluctance, endless provocation, dysfunctional everything. We weren’t burdened with problems so much as relentlessly bedraggled. And through it all, the client showed me the love. I couldn’t quantify it in the moment, but I absolutely, unmistakably felt it.

What did it feel like? Unstinting trust. Trust that we’d get there, trust in fast iteration, total trust in me – in who I am and everything I bring.[8] How did they create that? By being themselves on full beam – not inadvertently but with clear intention. And they never wavered. They never ran from the risk. I knew where I was with them: safe.

So when they eventually asked me why I hadn’t run for the hills, my answer was instant:

You showed me the love.

It wasn’t nice, or kind or cheering. Showing me the love was powerfully enabling. I didn’t need someone to hold my hand. I needed someone to have my back while I rebuilt the ship, held off the storms[9] and steered us to shore. And we got there. Verrrrry bruised, but with success in our sails. The power of love? I think so.

Impertinent Questions

Intrigued by the love? Feeling it, showing it, what is it? Let’s get curious with some impertinent questions. (Click here for an expanded, downloadable version.)

🤔 When have you felt the love?
How did you experience it? What did it enable in you? What did safety feel like?

🤔 Where do you notice the love?
Who elevates an interaction? What feelings are they channelling? How do people respond?

🤔 How do you show the love?
When do you make a difference by being, not doing? Which qualities do you dial up? What vibe are you creating?

Of course, you might show the love and… nothing. If so, don’t be downhearted. (But do get curious.[10]) Because whatever happens, showing the love sharpens your mettle. It exercises your muscle for risk. It clarifies who you are as a leader. It builds your confidence to show up with that clarity. Not hesitantly or inadvertently, but deliberately and courageously.

You can’t show the love indiscriminately. You’d be knackered. And probably too much. But also: there’s no need. So preserve it for moments that call for a different, deeper quality of connection. Like with those wary leaders, or that freaked out group, or me on that hazardous project. Because showing the love is special. It’s extra. It’s a hard-to-quantify superpower. What’s love got to do with it? Everything.[11]

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

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FOOTNOTES

[1] I used to send it to Coventry. Which wasn’t entirely silly then, but I’m glad I don’t now.

[2] With thanks to the very kind people who supplied feedback, examples and helped me wade through the mess!

[3] There’s a difference between actively figuring out and passively saying.

[4] Plus: every evening starts with sherry hour. What’s not to love?

[5] You can’t just announce a “safe space”. You have to create it, not least by communicating a feeling of safety. Showing the love really helps, because it asks you to be clear in who you are – and to meet people where they are (bleugh, brilliant, wherever).

[6] Which doesn’t mean taking up all the space. Or being an arse. (Personally, I like to save that for my family.)

[7] Being not just you, but you on full beam, can be terrifying. But ultimately, there’s less friction in being who you are than who you’re not. It’s clearer. It builds trust faster because people know what to expect. It’s probably what people value in you anyway. And you get further because the effort of masking can be redirected somewhere more useful.

[8] This was everything. I’ll never forget it.

[9] Other ‘s’ words spring to mind.

[10] It’s an excellent antidote. Refer back to your impertinent questions. What still sounds right? What doesn’t? How can you gather more evidence?

[11] What a woman, 100% showing the love. 🔥💪💔

What can you drop?

Yeah, you’re right, probably nothing. Or nothing you haven’t ditched already. Because everything matters. And even when it doesn’t, it feels like it does.

Which would be fine if it all fit neatly into the day with no awkward spillage either side.[1] It’s just that, quite often, it doesn’t. So something needs to give. But what?

Thing is, when you’re used to doing loads it’s quite the mindgame to do less. We can chant what got you here won’t get you there in unison, but it can still feel like doing less = delivering less. When actually, it creates space to deliver more that matters.[2] And the more ingrained that desire to do more, the harder it is to strike stuff off your slate.

Which is where one in, one out comes in. When the leaders I work with are overworked we agree that if they add something to their slate, they have to drop something else. (Which can’t be themselves.) Because yes, they’re remarkable but no, they’re not infinite.

So how to decide what’s for the chop? Get curious, of course!

What are your inexplicable obligations? 🕸️

Feel obliged to do something? Can’t find a good reason for it? That’s an explicable obligation. It’s a like being caught in a web which even the spider has thought “meh”, and buggered off.3 We all have ‘em:

Things you do because you feel you ought to
Things for which there’s no discernible reason beyond that’s how we roll
Things for which there is a solid reason, but not one that justifies the effort
Things you feel you ought to do, but don’t, but then spend so much time contemplating it would’ve been faster just to do them in the first place

Sometimes a fresh pair of eyes is all you need. Like when a leader I worked with joined a team and discovered that the entire week was scheduled in conference calls.[3] 😩 No one had time to do the actual job. She thought “WTF”, politely declined everything, and started again with just two calls. And reader: stuff got done.[4]

Yep, an extreme example. But inexplicable obligations are neither unusual nor the preserve of idiots. That team had plenty of smart, forward-thinking people, but their process was bananas. Or had stealthily become bananas.[5] That’s part of the problem with inexplicable obligations. They’re often so well absorbed into the bloodstream of process (yours, the organisation’s) that they barely register. So your energy continues to be sucked up by tasks that don’t pull their weight.

What to do? A timely WTF can help. Or just look at your slate and get curious:

Why should you do this now?
According to whom?
Does the end justify the means?
What or who does that end serve?

You’ll probably have solid, indisputable reasons for most stuff. But there’ll almost certainly be something you can’t quite pin down. For which your reasons are vague. Or, if you’re honest, a bit suspect. This is the stuff to inspect up close. Does it pull its weight? Or is it an explicable obligation that deserves to be ditched?[6]

Who is this for?

Maybe you did all of that, and everything’s still on your slate. Maybe, while asking those questions, you realised there was stuff missing from your slate so now you’ve even more to do. 😖

In which case, ask yourself: who is this for? Who benefits from it – and in whose eyes? Do your beneficiaries value their apparent good fortune? Or do they [deep breath] not actually care? If they do care, should they own the task instead? Perhaps because they’re more invested in it. Or perhaps because they value the outcome but need to understand what goes into it. And if they really don’t care then, well, should you?

Years ago when I worked at… no actually, I’ll keep that to myself. When I worked at [ahem, cough] a lovely colleague with a firm belief in transparency would keep us in the loop. With absolutely bloody everything. Cue REAMS of e-mails, with everyone ‘cc’ed.[7] And the thing is, we needed to know almost none of it. My heart still sinks at the recollection.

My colleague wasn’t doing this to entertain himself. He did it because he thought we valued it. He didn’t check that assumption, and we didn’t disabuse him of it. It just became an inexplicable obligation: for him to overload us, and for us to wade (resentfully) through the overload.

Of course some stuff is worth doing even though it seems unappreciated. But sometimes no one benefits, or not enough to justify the effort. So again, look at who benefits from any given task. Find out: ask people if that benefit’s real or imagined, and for whom. Then decide whether it deserves its place on your slate, or someone else’s – or, frankly, no one’s.

A note of caution.[8] You might conclude that something is of benefit, and could be done by someone else, but that you’ll do it faster. You might be bang on. But in itself that’s not a reason to hold on to it. You’re not the only person who deserves to build that expertise. Or to learn from a few cock ups. And besides, if you keep doing stuff that doesn’t belong to you, you’ll be forever squeezing the stuff that does.

Where are your ghosts? 👻

Not that sort. I mean the “legacy” projects, ideas, even full blown products that still lurk in your calendar. It’s often stuff you conceived and nurtured and walked through fire to get up and running. Stuff that had meaning, and purpose. Perhaps it even made you who you were. But it isn’t relevant to who you are now. And, moreover, to who you might become.

Like wot, though?

Sometimes you start something, it runs its course, and then lingers. A mate of mine used to run ‘un-office hours’. And continued to do so long after it’d stopped being useful to him. There it was in his calendar, week in, week out, blocking up time he could be using elsewhere. He ended up ignoring it, or working round it, but it was still occupying space in the back of his mind. Until he finally ditched it. Phew.

Or sometimes you build something with huge potential – that’s never quite reached. One leader told me about an innovation project she’d worked on that could’ve been game-changingly brilliant. If people had wanted it. They didn’t. But the whole team was so invested they wouldn’t let it die. Thing is, I get that. Sometimes you do have to bide your time. Sometimes you do need to show grit and determination. And sometimes you just have to let it go so you can do something better instead.

FWIW, I think it’s bloody hard to give stuff up. Even more so if it once meant a lot to you. Closing my beloved choir seven years ago felt like exactly the right decision at the right time. But it was still a proper wrench. Likewise, an entrepreneur I know recently handed on the book group he founded 12 years ago. Then, it had been his escape from the madness of starting and scaling a new business. Now it was sucking the joy out of reading.

Some ghosts are easy to spot. A quick squiz at your calendar and they whack you in the face. Others are more resistant to daylight, lingering in the uncertain realms of ‘but’ and ‘maybe’ and ‘if’. Be brave. Slip on your proton pack and fire off some impertinent questions. After all, what have you got to lose? More to the point, what can’t you afford to keep?

🤔 Get curious about what you can drop with 5 impertinent questions

It’s not always easy to start, but impertinent questions can help. Download ‘em here. Try applying them to your schedule over the next fortnight, and run experiments on your assumptions. What actually happens when you drop, delegate or ditch altogether? Drop me a line and let me know! (I love hearing from you, I’m nosy. Etc.)

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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[1] And we’re off with the caveats! First up: maybe it does fit neatly. Maybe you thrive on the no-distinction between work and not-work. Actually, isn’t that a Gen Z trend, what with the whole digital nomad thing? Or are we just telling them it’s something they aspire to in the hope they don’t notice that being a nomad is your only option when you can’t afford the rent?

[2] Because, for example, it’s of higher value to the business. Or because it’s more relevant to your team. Or because it makes your heart sing.

[3] This was well before Zoom, so they were old skool calls down a scratchy phone line. Fun times. 😭

[4] Although not everyone was happy about it. Changing stuff, and particularly dropping stuff, can ruffle feathers. But that’s not a reason not to do it. Just don’t be a dick for the sake of it.

[5] Stealthy bananas! 🤣 Anyone? No? Just me then. 😳

[6] Ooh! I'm going to start something called The Ditchery. A repository of stuff that bites the dust. Send me yours!

[7] It wasn’t everyone. It was about five people. It just felt like everyone, especially when we all felt obliged to reply and add to the inbox madness.

[8] Or rather, another note. Everything I write is drenched in caution ­– I bloody love a caveat!

When are you a high performance procrastinator?

How’s your to-do list? Ticked off like a trojan?[1]

Here’s mine:
✅  Set client strategy
✅  Design big presentation
✅  Catch up on industry news
❌ Write newsletter

So yeah, my actual top priority was to write this. But look! I accomplished Lots of Other Stuff. No slackers here, amirite?!

Thing is, we often think of procrastination as making more tea, endlessly refreshing e-mail, or tidying a spotless desk.[2] In other words: conspicuous avoidance. But for the leaders I work with, that’s mostly not what procrastination looks like.[3]

Their avoidance is often inconspicuous, in the form of prioritising other core tasks. Because when everything feels urgent it’s hard to privilege importance. And besides, you’re still busy. You’re still working hard. And you’ll still deliver… Just with more friction and less energy. (Like this newsletter. 😬)

Are you being productive or performative?

Inconspicuous avoidance is hard to admit. Because from the outside, busy is busy. Only you can really know whether you’re very busy with one thing because you’re avoiding another. A friend of mine calls this ‘high performance procrastination’.[4]

Which is bang on, isn’t it? To the all the world it looks like you’re working terribly hard. And indeed you are. Just on something else.

So it’s worth getting curious about whether you’re being productive or a high performance procrastinator at any given point. Sometimes just noticing can nip it in the bud:

Does this require your urgent attention?
Does this deserve your best energy?
Does that deserve the dregs?
Are you, just possibly, shooting yourself in the foot?

You could ask these and other questions. Except probably, you already know. You know whether you’re practising diligence or avoidance, even when they look alike. And you know what you’re avoiding. So then what?

Why are you procrastinating?

What’s behind your not-so-classic avoidance? Fear?[5] Or boredom? Or ‘this is really difficult and requires best-brain and all I can summon is bleugh-brain’? (For which I tried to come up with a snappy label, but failed.[6])

Or are you, most unhelpfully, procrastinating because it really matters? It might sound odd, but really wanting something can have a paralysing effect.[7] Because: what if you actually got it? Then what? Who would you be then? 😮

This sort of procrastination often gets muddled up with fear. But it’s not quite the same. Yes, there’s a nervy anxiety to it. But in my experience, it tips towards feeling unready more than scared. And that makes holding off seem smart: surely more prep = more ready. And yep, that's true. Until, of course, you miss the boat and render all that prep futile.[8] 🤦‍♀️

But how to get back on the wagon?

It’s all very well knowing what’s behind your procrastination. But then what? Sometimes a firm eyeroll is enough. And sometimes an impertinent question can help.

Is it boring?
What could add a spot of levity?
Which incentives might make it more palatable?
Where might joining forces make it easier, funnier or, ahem, fun-er-er?

Is it difficult?
Where can you apply what you already know?
How can you channel shitty first draft energy?
How can you chunk the madness with One Step Forward?

Does it really, deeply matter?
When will you be ready?
What if it doesn’t work out? What if it does?
What if you gave yourself a friendly but firm shove?

Will this eliminate procrastination? Nope. Can noticing the niggles help you answer them? Or crack on anyway because they’re unanswerable? Yep. Will they pop up again? Of course! But it’s easier to dismiss that but-but-but when you’ve previously batted it away.[9]

But wait! Can procrastination be a good thing?

Strap in: about turn ahead![10] Sometimes it is smart to procrastinate. Sometimes you need a break. Sometimes you need other stuff in place first. And sometimes what you’re supposed to be doing loses saliency, while what you’re not doing rockets in appeal.

On which: if both tasks are of equal importance and urgency, there’s no harm in switching. You might even save time by harnessing your intellectual energy more efficiently. But it’s not without risk. An unexpected event can throw everything out. So switch, but don’t luxuriate.

There’s another way in which high performance procrastination can be smart. Sometimes the thing you do instead is just… better. A friend of a friend has a corking example: their now multimillion dollar business was born out of avoiding their novel. See? Avoidance really can pay off![11]

(It’s just annoyingly hard to plan. 🙄)

If you get it done, does procrastination actually matter?

Well, yes. Perhaps not to anyone else, but almost certainly to you. High performance procrastination is still work. It still uses energy and brain power. It still leaves you tired after a long day. But it’s work stripped of satisfaction, progress and potential fulfilled.

Most leaders I know need that internal validation. Because it’s not just external delivery that matters; it’s how that impacts your sense of self. And too much high performance procrastination can chip away at that.

So allow yourself a massive sigh. And then privilege what matters with your best energy, not the dregs.

And with that, I’m off to do nothing – busily. 👋

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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[1] Of the determined rather than viral variety.

[2] I actually long for a spotless desk. Emma Cownley of Jot Jot Boom cleans hers every weekend. I am in awe.

[3] No one I’ve met is immune to conspicuous avoidance; they just don’t do it at work.

[4] Thanks, Nick! That did, indeed, explain things.

[5] That fear might be of the actual thing – delivering a conference presentation because you have social anxiety, for example. Or fear of failing at the thing – like delivering a crap presentation. It might even be a fear of being found out – the shame of everyone realising you’re a, I don’t know, “presentations fraud”, say. (And no, I don’t know what one of those is either. Which is the point.)

[6] Although ‘can’t be arsed’ comes close. Bit harsh? Perhaps. But honestly, haven’t you felt that sometimes?

[7] And besides, who isn’t a contrarian at heart?

[8] There’s so much more to say about this, about how fear intersects with hope, and the mental gymnastics of getting what you want. I might even write a post on it. Mañana.

[9] But-but-but… is it really? Yes. Incidentally, this tends to be more fun with someone else. There’s something freeing and funny about saying it all out loud. Daylight might be a disinfectant, but so is laughter.

[10] See 7.

[11] How can you know whether it’s worth the trade? You can’t. But you can get curious if you feel inexorably, relentlessly drawn to something. Or conversely, relentlessly downhearted. What is the pull factor, and the push? Is it temporary or persistent? How could you find out more: who could you talk to; what could you start to test out?

[12] Yep, another glorious segue. Working in telly really did set me up for anything. 😂

Where could you be more crap?

Are you good at life? Could you be better? I’ve devoted hours to this elusive goal. Better at mindfulness. Better at writing newsletters. Better at being… better.[1]

Being better is, basically, leadership law:

Continuous learning
Executing
Innovating
Everything-ing

Even being better at failing. (Yep, apparently it is possible to fail at failure.)

Isn’t it good? Well yeah, maybe. But God, it’s exhausting. So much effort goes into being better. When do you get to be crap? I don’t mean feeling you’ve been a bit crap. Or that you haven’t done your best. I mean being crap on purpose.[2]

But… why would you? 🤯

Well, partly because there’s something liberating about not even intending to be great. And partly because, however marvellous you are, you won’t always add value.[3]

But also because not everything matters. At least not in the same way to the same extent at the same time. And figuring out what doesn’t matter leaves you more room for what does.

Also, whisper it, sometimes you just will be… a bit crap. 😱 So, to the extent that you can, you might as well be crap on purpose. Selectively, deliberately, and where your brilliant brain won’t make a difference.

Hang on a minute, what does that even mean?

Good question. What does being crap mean?

Is the outcome subpar?
Is the outcome fine but the expectation sky high?
Is the process less effort?

These are different things. They require a different response. And they can unfold in confounding ways. Fantasy expectation can obfuscate real need. Un-crap effort can produce a crap outcome.[4] And less effort can improve an outcome.[5]

And then, of course, there are degrees of crap. Sometimes more is more; sometimes it’s just meh. Sometimes the quality of attention is the difference between brilliance and balls-up.

But we often lump it together under one crap umbrella. Which isn’t helpful. So get curious instead. What does being crap mean in this context? What does it mean to you? What does it mean to someone else?[6] And: why?

It’s worth running a few experiments to figure this out. To gauge what being purposefully crap feels like. To sensitise yourself to its various qualities. And to find out where and how you could (or shouldn’t) be more crap. Here are three places you might start.

1. Where do you excel?

Excellence is satisfying. It makes us feel valuable.[7] Which makes excessive effort so enticing. But beyond a certain point, does being even more excellent make a difference? Does it serve you? Does it reduce your attention for other stuff? Could less effort in the process – being “a bit crap” – free you up elsewhere?

Run some experiments where you excel. Which bits of a task require your brilliance? Which just need competence? Where could you give less – perhaps in thinking time, detail or extras? What actually makes the difference? Your less will probably still turn out to be more.[8]

Get curious, too, about what’s actually valued. You might discover your extra effort isn’t. Or gets in the way. Which can be annoying, and disheartening, and more fool them, etc. But it’s also useful data in deciding what deserves best-brain. And what doesn’t.

2. Where do you secretly fear crapness?

Enough of excellence. Where do you give too much for fear of being not enough? What do you fear might be revealed without such diligence?

Fear might be essential, even enjoyable. But it also provokes all manner of peculiarities. Like going the extra fifty miles instead of one. Or ploughing in hours of thought where two would do.[9] Because if you didn’t, who knows what might emerge? 😬

Put your secret crappiness to the test. What happens if you ease off a bit? Where can you ease off? Where do you need to make more effort? What’s the sweet spot between underdone and overblown? Or between your fear-filled expectation and actual need?[10] And does your fantasyland perception of "crap" baffle everyone else?

3. Where does it just not matter?

The day other day, my (very patient) niece gave her (not very patient) aunt a cello lesson. Said aunt had always assumed an affinity with the cello. Sure, there’d be the odd duff note. And third position might be a stretch. No matter. She’d be singing out Elgar’s Cello Concerto in no time.

Reader, it’s true. I was singing the concerto in no time. I just wasn’t playing it. Turns out I find the cello both quite tricky and verrrrry painful.[11] I wasn’t just a bit crap. I was utterly crap. I couldn’t trap the strings. I played all over the bridge. I could barely hold the bow.

BUT

It was really fun! Because none of it mattered. Who cares if I suck at cello?[12] Not even me, despite my massive ego.

The thing about my job, and probably yours, is that there’s not much opportunity to be overtly crap. To be deliciously, delightfully rubbish. To revel in hilarious, abject failure precisely because it doesn’t matter. To care about process instead of outcome and notice how that feels. That’s hard in the whirl of work.

Which is a shame. Because actually, being deliberately crap is incredibly freeing. Sure, you might learn something. You might even discover a new talent.[13] But that’s not the point. It doesn’t matter. Literally no one cares, including you. Phew.

So again: get curious. What does being crap mean, and when, and why? Where is best-brain not required? When is effort driven by fear? How can you trade less effort on what doesn’t matter for more on what does? Where does being crap free your soul? 🥳

This is how to be more crap.[14] Not blithely and wholesale. But discretely, purposefully and, with a spot of luck, hilariously. So go on, kick up a stink! 👋

Keen to get curious and fancy a spot of help?

Get intensely curious about who you are, who you’re not, and what actually matters with Impertinent Questions. My nosiness meets your context each weekday for a month.

Get curious with The Curious Leader newsletter direct to your inbox. Longform, practical, personal opining on curiosity in leadership. Like today’s on FOBFO-busting, or this one on owning your success.

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 [1] Perhaps I should apply for BBC Director of Better.

[2] I’m currently in hostage negotiations with the “delivery” “service” Yodel, which has hijacked my parcel. Serious commitment to ‘be more crap’, there.

[3] And might make it worse. By redirecting attention towards you. Or asking redundant questions. Or squashing someone else’s opportunity. Or…

[4] I know, so unfair.

[5] As above.

[6] Like this morning, when a friend with an actual degree in maths described himself as ‘a crap mathematician’. 🙄

[7] And no wonder. More effort + more talent = better results is a very sticky notion. And makes more talent + tiny effort = same results seem terribly unfair. Although the hard work + talent = success equation collapses anyway because it’s so often trumped by privilege = success. Which isn’t to suggest you can’t be talented and hard-working and privileged (👋). Or a privileged distaster. But you won’t have to be as talented or as hard working to get further than someone with less privilege. Tricky, but true.

[8] Just don’t be a wally.

[9] Fear also provokes avoidance. On which: this.

[10] Years ago I spent fear-stained hours perfecting practice tracks for my choir. Just in case they weren’t (tr: I wasn’t) quite good enough. Pointlessly, as it turned out: they only ever got a brief, half-arsed listen anyway. So now they’re crap. I record one improvised version, and that’s it. Doing them quickly and crappily has saved me buckets of time. And: no one cares! 🤦‍♀️ Plus I preserve my energy for rehearsals, which is where my best brain really matters. (And where I change everything anyway.)

[11] Tragically, my callous heart hasn’t extended to callused fingers.

[12] Possibly the neighbours.

[13] I haven’t. But my kind niece has agreed to another lesson. I have agreed to be better behaved and less impatient. Unclear which will transpire.

[14] Has this post become unintentionally meta? 😬