Have you forgotten what hard feels like?
Readtime: 3 minutes
The higher you go, the easier it is to forget how much effort some things you ask people to do will actually take.
It happens so gradually you don't notice. And by the time you're three levels above the work, your sense of what it takes to do it is almost completely detached from reality.
Here's what it looks like.
You send a message at 4pm on a Thursday:
"Can you pull together some numbers on this for tomorrow?"
It takes you 30 seconds to type. It takes someone three hours to do. And they probably won't leave on time tonight because of it.
I saw this from the other side earlier in my career. I was a senior manager at KPMG, sitting in a Board committee meeting at a major client alongside the lead partner. In one sentence, he offered to report some data to the committee every quarter. To him it was a small commitment. In practice, it would have meant collecting information from every KPMG firm worldwide that had worked with this client – and our systems didn't track it.
Weeks of work every year for a nice-to-have.
I spoke up and suggested a simpler alternative, which fortunately people were happy with. But that one sentence nearly committed us to something nobody in the room understood the cost of, except the people who'd have to do it, i.e. me!
This isn't a complaint about senior people. It's just what happens naturally as you get further from the work.
The everyday tasks – the ones you now delegate in a sentence – used to take you a full day. But you've forgotten the learning curve, the uncertainty, the three false starts before you figured out the right approach.
When you've done something a hundred times, you instinctively know how long it should take. But that's how long it takes you now, with 20 years of context. Not how long it takes someone doing it for the third time, who also has to figure out which stakeholders to consult with, which template to use, and check whether the inputs are still right.
The irony is that the better you've got at your job, the worse your instincts are for estimating what it takes someone else to do it.
And here's the part that makes it worse. Most people won't push back on your timeline. They'll just absorb it. They'll work late, skip lunch, rush the work, or feel like they're failing because they can't do it as quickly as was implied.
You'll never find out, because nobody tells the senior person that the deadline was unrealistic. They just try to meet it.
Remembering is a leadership skill
Which is why I think remembering what it was like is one of the most underrated leadership skills there is.
Not remembering nostalgically. Remembering practically. The anxiety of a vague brief. The stress of an unrealistic deadline. The fear of asking a question that might make you look stupid. You lived through all of that. And that memory – if you use it – makes you better at setting people up to succeed.
Teams trust leaders who remember what it's like to not know yet.
Stay connected to what's coming
And there's another dimension to this. Everything you know is frozen in a moment in time. The way you learned to do things, the tools you used, the norms you grew up with professionally – all of that is slowly becoming less current.
Which is why I think it's worth surrounding yourself with people who are younger than you. Not as a mentoring exercise – although that's valuable too – but as a guide to other and better ways of doing things.
Younger people are more alive to how work is changing, how communication is changing, and what good looks like to the next generation of clients and colleagues. If you only spend time with people at your level, you lose that signal.
This point connects back to the same idea. The more time you spend with people earlier in their careers, the better your memory stays. You see what's hard for them. You see where your assumptions are outdated. You stay calibrated.
Something worth trying
So here are two things to try this week.
First, next time you're about to ask someone for something, pause and ask yourself: how long would this have taken me in my first year of doing it? Then set the deadline based on that, not on how long it would take you now.
And if you want to go further, ask someone on your team:
"Is there anything I've asked for recently where the timeline felt unrealistic?"
The answer might be uncomfortable. But the conversation will tell you more about your leadership than a lot of other feedback you get (or don’t get!).
The best leaders I've worked with don't just remember what it was like to be more junior. They use that memory every day – in how they set deadlines, how they frame requests, and how they treat the people doing the work they used to do.
Aim to be one of those leaders.
Thanks for reading.
Mostyn
P.S. If you’re not quite at the top yet, but on your way, then you’ll love my new YouTube video: Professionals Who ACT Like This Get Promoted Fast