Hi Reader

(3.5-ish minute read..you'll love this edition. Promise.)

I was presenting a new sales strategy to a sales team I was working with as a fractional Sales Director.

All the usual content; a fresh approach, significant change, resources being allocated etc and, to be fair, considerable work had gone into it.

I wrapped up the 15-minute presentation and then asked something that visibly surprised them (maybe it was more shock than surprise actually).

The room went quiet.

You know that quiet, the one here you think nobody is actually breathing?

That's what we're talking about today.

Amy Edmondson, who's spent decades researching why employees stay silent about problems they can see, puts it plainly:

Note, your problem. Not their problem.

You see, when your people aren't telling you what's broken, what won't work, what they're worried about, then you've built something. Sadly, it’s just not what you think you've built.

You probably think you've built a high-performance team.

Sorry, you’ve actually built a compliance culture where people have learned it's safer to watch things fail than to speak up before they do.

The worst part is that you probably did this without meaning to.

Research from organisational behavior studies found something that should terrify every business founder: 85% of employees report feeling unable to raise concerns with leadership.

However, here's the part that stings like a nettle: in 70% of major organisational failures, post-mortems revealed that multiple team members had identified the critical problems months before collapse but stayed silent.

If you read no more of this newsletter today then this alone is worth it….your team can probably see what's about to break but they're sitting there just calculating whether telling you is worth the risk.

Unsettling isn’t it?

I've used Canva for years but I only properly understood their culture recently.

Melanie Perkins built Canva from a university dorm room idea into a $40 billion company by doing something most founders struggle with: she made it safe to fail publicly.

Early in Canva's growth, the team invested heavily in a collaboration feature they were convinced would be transformative. Months of engineering resources. Leadership fully committed. Then someone, and in psychologically safe cultures it's always someone who wouldn't have spoken in a different room, said what needed saying:

They were right. The feature launched and…..silence. Six months of development time and considerable opportunity cost on features users actually wanted, gone.

What matters here is not the failed feature but what Perkins did with the moment. She made the challenge 100% visible instead of just tolerating it. She signalled explicitly that speaking up, even against leadership's most cherished assumptions, was exactly what the culture required.

Now Canva has a Fail Wall where team members share failures and lessons publicly & regularly, without blame. Perkins herself shares the stories of the 100+ investors who rejected her. Her pitches that bombed and her assumptions that proved wrong.

Of course that’s not a policy, just a leader going first.

When you're scaling from thousands of users to over 100 million you can't afford to repeat expensive mistakes. You need people finding problems early, speaking up about concerns, challenging assumptions before they become catastrophes. That goes for a growth-stage company every bit as much as a $40 billion one.

And that only happens if speaking up feels safer than staying quiet.

An example from my own experience: I had the opportunity to work with a founder a while back. They’re Series A funded, €3.2M raised, eighteen months to hit Series B metrics or face a down round.

Regularly I’d hear her asking the team: "Why didn't anyone flag this earlier?"

The background detail here is that it was three months into the year, they were tracking at 43% of revenue target. Sales cycles that were forecast at 45 days were averaging 87 days. Enterprise deals kept stalling at legal review. Monthly churn had crept from 3.1% to 6.8%.

So she had a valid question but the wrong frame.

More than two people had actually flagged it. In different ways and at different times.

The Sales director mentioned it in a January conversation. Something to the effect of "I'm concerned these enterprise timelines are twice what we modeled." The response: "We need to push harder, can't afford to miss targets."

The Head of Customer Success then raised it in February. Not verbatim but to the tune of "The assumptions in our retention forecast might be optimistic given what I'm seeing." The response: "Let's stay focused on execution, we'll review metrics at quarter end."

There were other similar examples. Nobody got punished & nobody got fired. Nobody even got criticised.

But nobody got heard either.

So they all stopped trying. Things became performative and they watched the numbers deteriorate. They knew the Series B metrics were becoming impossible but they stayed quiet because speaking up had proven pointless. Could you blame them?

When the founder finally acknowledged the problem in May, she'd burned five months of runway on a strategy her team had been trying to tell her was broken since January.

Every action has a consequence and the cost here could well be the difference between a Series B and a down round.

I know from a long career in sports performance leadership that a really rewarding and profitable coaching philosophy can centre on one just thing: building and maintaining trust.

How did you engineer that?

One core element is relentlessly honest feedback.

Most founders & leaders think they want honest feedback. In my experience, what they actually want is validating feedback delivered gently.

Because real honesty is uncomfortable and it stings. Most of the time for both people.

Say someone telling you your strategy has holes or your pricing is wrong or your best & most favoured salesperson is destroying team morale. Or that your growth projections are fantasy.

Your response in that moment, not what you say but what people feel after saying it, determines whether anyone tells you anything useful again. They remember how you made them feel.

You probably think you're approachable, open and the kind of leader people can be honest with.

But maybe your people are reading different signals?

Maybe they’re reading the times you said "I hear you" then didn't change anything. The times you asked for input then reacted immediately and defended your position for twenty minutes. The times someone raised a concern and you jumped in to explain why it wasn't actually a problem.

Each one of those moments taught them something: around here honesty is tolerated but not valued. Speaking up creates work for them and annoyance for you. In the end, smiling, nodding and staying quiet is easier.

And you're confused why nobody tells you things until it's too late to fix them?

There's this phrase that gets thrown around a lot about creating "psychological safety" and I'm wary of it because it's become jargon that people nod at without understanding what it actually requires.

Edmondson's research found we're hardwired to worry about impression-making in hierarchies. This simply means your people are constantly calculating: "Will saying this make me look stupid? Negative? Not a team player?"

If the calculation comes up "yes" or even "maybe," they stay quiet.

You can't just go along with the usual No.1 bullshit and declare "we have psychological safety here"....and expect people to just believe it. You build it, and earn it, through repeated evidence that speaking up doesn't have costs.

It’s hard work and there's a tricky bit worth flagging. It's not about creating a soft environment that doesn't demand high standards. That's not safety, that's lowered expectations.

Real safety is being able to say "I think we're wrong about this" in a culture that still demands excellence. Those two things have to coexist. That’s high-performance.

The founder I mentioned above? Once she understood the pattern, she changed one thing.

At the next team meeting, she asked: "What am I not seeing that you are?"

Then she went quiet and waited. She sat nervously through the properly uncomfortable silence and waited some more. Of course, nobody wanted to go first.

Finally, her sales director, the guy who'd raised concerns in January, said: "Our enterprise deals are stalling because we're not addressing procurement and legal concerns early enough. We're treating them as sales blockers instead of building them into the process from the first conversation."

Her response would determine everything.

She could have said "Oh, we addressed this in the sales playbook" or "That's why we have the legal template" or "Let's take this offline."....or some other jingoistic piece of jargon.

What she actually said was,

Next, a twenty-minute conversation revealed their entire enterprise motion was structured wrong. They were running a transactional sales process for deals that required consensus-building across procurement, legal, IT, and end users.

So they rebuilt the approach within a few weeks. Enterprise cycle times dropped from 87 days to 52 days and in the next quarter they hit 91% of revenue target instead of 43%.

The cost of not asking that question in January instead of April was three months of time burned, around €400K in deals that stalled, and Series B metrics that went from aggressive to fantasy.

As always, let's end with the beginnings of a solution to address this issue in your own environment.

When was the last time someone on your team raised a concern about your strategy, your decision or your plan?

What did you say? More to the point, what do you think they heard?

Did they walk away thinking "Great, that was heard and valued" or "Oh, that’s just being filed away again in the ‘for info’ file"

Because I know they're making that calculation constantly and every time they think about speaking up, they're weighing: "Is this even worth the risk?"

If the answer keeps coming up "not really," you've built a team that watches problems compound while staying quiet about them.

Canva didn't become a $40 billion company because they never made mistakes. They made loads. Don’t we all. The collaboration feature nobody used was one expensive lesson. But they made it visible, took the learning and, in the future, moved faster & more agile because of it.

Your team already knows what's broken. They know which assumptions are wrong. They know where execution is failing. They're living in that world daily.

The concern at hand is whether they think telling you is safe enough to bother.

You signal the answer to their question in every interaction, whether you realise it or not.

The Commercial Thread:

Revenue forecasts live or die on whether your sales team tells you what they're actually seeing in deals versus what you want to hear. If your commercial/sales people have learned it's safer to be optimistic than honest about pipeline quality, deal timelines, or customer objections, your forecast is fantasy. The "tell me why this won't work" question applies directly here: when did you last explicitly ask your commercial team to challenge your assumptions about what's driving or blocking revenue? And what did they hear when they answered?

Another Newsletter you might find useful....

Helping Leaders Level Up Their Impact By Beth, an expert in leading through layers and building strong teams Leadership can be exhilarating and isolating--sometimes in the same hour! Twice a week, I share practical insights and real-world stories to help you tackle challenges with clarity, strengthen your team, and grow into the leader you want to be. Subscribe​

Thank you for being part of this community of Leaders. The work on how to lead better is something you have to do alone. But you don't have to do it on your own. Onward and Upward, Paul Clarke https://www.paulclarke.iehttps://www.linkedin.com/in/paulclarkeperform/​

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