You don't have a time management problem. Why senior leaders never have enough time.

Nobody decides to have this many meetings

I spent several years at Shopify. It was one of the fastest-moving companies I have ever worked in. We used to say we were building the plane while flying it. Priorities changed every week, teams changed, products changed, and most of it happened remotely. In that kind of place communication matters, so you have a meeting. Then the meeting becomes weekly. Then someone else needs to be there. Then there is a pre-meeting.

Nobody sits down one day and says, "Do you know what would make this company better? A thousand more hours in meetings." It just happens. One reasonable decision at a time.

In January 2023 Shopify did something radical about it. It deleted around 12,000 recurring meetings from people's calendars, brought back no-meeting Wednesdays, and asked everyone to wait two weeks before putting any recurring meeting back (CNN, Bloomberg). People came back from the Christmas break and their meetings were simply gone. My first reaction was, what are you doing?

What I came to respect was the way they did it. They didn't ask people which meetings they would like to cancel. Everyone would have defended the meetings they already had. Of course I need that one. Finance needs to be there. Product needs to be there. Instead the default flipped. If a meeting really needed to exist, you could bring it back, but first you had to live without it and justify it.

If you don't interrupt it, yesterday's decisions quietly become today's obligations. And eventually today's obligations become tomorrow's culture.

The lesson is not that meetings are bad. Plenty of them are valuable. The lesson is that defaults are powerful, and once something is normal we stop asking whether it still serves us. Someone at Shopify was willing to ask, "Why are we doing all of this, and what would happen if we stopped?" That is a leadership question, not a productivity hack.

Parkinson's law is only half the story

In 1955 the historian Cyril Northcote Parkinson wrote that work expands to fill the time available for its completion. Give someone eight hours for a task and there's a good chance it takes eight hours. Give them two and they often find a way. I put my hand up. I'm one of those people, as I admitted on Everyday Leadership.

Picture a whole day set aside to prepare a presentation. You check email, do some research, read something a colleague sent that is only half relevant, tweak slide three, ask someone what they think, change slide six, have lunch, answer another email, make another revision. At five o'clock it's finished.

Now picture the same presentation at 11am with two hours' notice. Once the panic passes, you start asking better questions. What does this audience need to understand? What are the three things they must know? What decision am I asking them to make? What can I leave out? Same person, same intelligence, very different constraint. The constraint created the clarity.

That's the part of Parkinson's law I care about. Not how to squeeze more work out of people, which we have tried for years and which doesn't work, but what becomes visible once you remove the luxury of unnecessary complexity.

It helps to separate three things that get used as if they meant the same. Productivity asks how much you produced. Efficiency asks how well you used your resources to produce it. Effectiveness asks whether you produced something that mattered. You can be very productive and very efficient at something that should never have been done. There is no prize for becoming brilliantly efficient at wasting your own time.

Sometimes the problem is your relationship with the work

A senior leader I worked with had someone on their team who kept missing deadlines on an important piece of work. It had been outstanding for months. There had been conversations, extensions and plenty of flexibility. Eventually the leader set a hard line: three days, or someone else takes it over. The work arrived. Not perfect, but it arrived.

The easy reading is that this person only performs under pressure. I wasn't interested in the easy reading, so I asked a different question. What changed? Their capability didn't jump in three days. Maybe the outcome was finally clear. Maybe the consequence was. Maybe the short deadline left no room for overthinking. Maybe fear created movement. Maybe the original deadline was never taken seriously because nothing happened when it was missed.

Those are completely different explanations, and each one calls for a different response. If you decide the person needs pressure when what actually moved them was fear, you build a way of managing them that can't last. If you decide they need micromanaging, you solve their productivity problem by creating a workload problem for yourself. That isn't leadership. You have just moved the inefficiency onto your own desk.

Your interpretation drives your decision, your decision drives your behaviour, and your behaviour produces an outcome that often confirms the interpretation you started with. CEOs fall into this loop as often as founders do. "My team can't make decisions without me," so the leader steps into every decision, the team keeps bringing problems, and the leader says, "See? I told you." Except the team may simply have learned not to decide, because every time they tried, the decision got changed. I've written more about that pattern in the founder bottleneck.

Two overloaded leaders can need opposite fixes

Not every leadership problem is psychology. Sometimes a workload problem is just a workload problem.

I had a conversation with a senior leader whose organisation had noticed they were overloaded and reduced their working hours. It sounded caring. But the responsibilities, demands and competing priorities stayed exactly the same. They now had less time to do the same job.

They did not solve the problem. They compressed the problem. You cannot solve a capacity problem by giving someone a better calendar.

Part of the fix there was organisational: what should stop, what should move, where more capacity was needed. Part of it was personal. As support arrived, could this leader let other people do things differently? Could they set guardrails instead of overseeing everything? Could they tell the difference between "this isn't how I would do it" and "this isn't good enough"? Those are very different sentences.

So when two leaders tell me they're overwhelmed, I don't assume they need the same thing. One may need to stop controlling everything. The other may really be doing three people's jobs. One needs better boundaries, the other needs the organisation redesigned. One needs to delegate, the other already has. This is where generic leadership advice frustrates the living daylights out of me. Just delegate, just prioritise, block out thinking time, learn to say no. Fine. I've said all of those myself. But if they work, why isn't this person doing them already? The gap between knowing what to do and doing it is what I call the Intention Gap.

What do you believe makes you valuable?

This is where it gets uncomfortable. Finish this sentence honestly, based on your behaviour rather than what you think you should say: I know I'm valuable when...

People need me. I'm solving problems. I'm busy. I'm working harder than everyone else. I'm the one with the answer. I'm in the room where it happens. I'm copied in on everything. I'm fixing, rescuing, delivering.

Then ask where you learned that. Childhood, a first manager, a place where hard work was how you survived, years of being rewarded for stepping in. That belief may have served you brilliantly. The question isn't whether it was wrong. It's whether it is still useful, because you might be working very hard to prove a kind of value that the next level of your role needs you to express differently.

Your value used to be having the answer. Now it may be building the conditions where other people find it. It used to be solving the problem. Now it may be deciding which problems deserve the organisation's attention. It used to be doing more. Now it may be getting clear about what shouldn't be done at all.

Which leads to the question most people avoid: what are you prepared to stop doing? I don't enjoy that question either. My own CEO clients have turned it back on me. Everyone wants more strategic thinking time. What are you taking out of your calendar to get it? Everyone wants their team to take more ownership. Which decisions are you handing over?

A seven-day experiment

You don't need to delete 12,000 meetings. You might need your own small version of what Shopify did: deliberately interrupting something you stopped questioning.

For the next seven days, watch where your time goes. Pick one recurring activity that takes a meaningful amount of it. Then ask yourself four questions.

• If I had half the time for this, what would I do differently? What would I remove, prioritise, delegate, and what would still have to happen?
• Why am I not already doing that? Is it a real capacity issue, a capability gap in the team, fear about quality, habit, control, a conversation I'm avoiding?
• What does my current behaviour suggest I actually value? Not what I say I value.
• What is the one decision that would change the behaviour?

If you're a CEO or senior leader, take one recurring meeting and ask what decisions it produces. If nobody can answer, you have learned something. If you're a founder, try it on one recurring decision that still needs your approval. If there's a good reason it needs you, keep it. If not, name who should own it, agree what good looks like and when it comes back to you, and then step away.

Your calendar is evidence. It tells a story about what you prioritise, what you avoid, what you feel responsible for and what you refuse to let go of. In the end the calendar isn't the problem, it's a symptom, and the deeper question is what created it.