SEPTEMBER 17, 2026

You can’t prepare enough for some rooms

Tell me if you can relate to this scenario. You have a meeting with your boss and peers, or your board, or a business review with other teammates and senior leaders. They’re scheduled regularly but require a new set of slides to present and preparation to answer questions that anyone in the room can ask, yet you have to answer in front over everyone else.

Because of the amount of follow-up information that could “possibly” be asked for, by people with considerable power and reputations, you could spend an entire week preparing, and still leave feeling that you should have done more.

There’s no doubt you know your stuff, having done the job everyday around which they are asking for updates and forecasts.

You know the material and have checked the numbers, and asked your team to check theirs. And you’ve gone over the power points repeatedly, asking your team to review their contributions.

Then someone in the meeting asks about a detail several layers below the decision at hand, and suddenly that issue becomes the main topic of the gathering.

As you leave, you’re thinking to yourself whether these meetings are adding value for the job itself or just another exercise in public exposure in front of higher-ups. But no matter how you feel, you know another review like this is right around the corner when all you really want is to be able to execute your day-to-day operations, get back to your customers, and be left alone to just think before having to worry about “reporting out.”

Recently, two different coaching conversations surfaced this situation and showed me that these days, it doesn’t matter your industry, your business or even your seniority; everyone has a boss (even CEOs report to the board) and keeping others informed while they get to ask anything under the sun is a never-ending part of corporate life.

One investment management leader told me how much time he spent walking his board through materials to get his team’s deals authorized. The act of constantly reviewing each step with them, left little time to actually run the fund and evaluate the investments at hand. Yet in his mind, he also couldn’t just delegate the preparation to his team, without sacrificing quality or speed given his higher level of familiarity with the deals.

The situation really triggered his fear of failing. His livelihood depended on this job. And even if he managed to get his deals approved, the market could move against him and still lead him to derail. So here was someone who was damned if he did, damned if he didn’t. Over-prepare and have a shot at excelling in the eyes of the board and investment committee, but have no life or agency over his own time. And still maybe make some bets that would lose.

Or he could let go of the need for everything to be prepared perfectly, and potentially sacrifice his credibility if his team wasn’t able to step up and fill any gaps.

That very same week, a second client of mine, in a technology company described her boss as someone whose detailed reviews consumed an enormous amount of the leadership team’s time. A different industry than the first client, yet the same amount of pressure to explain the business internally, when they believed more attention needed to go toward customers and execution.

Putting these conversations beside each other, I was struck by how easily conscientiousness can turn a difficult situation into an endless personal assignment.

We can always prepare more, and check again, and add another layer of detail.

And when we do, since these are familiar actions with some aspect of meeting others’ expectations, they bring a deceptive satisfaction of having done something in our control, to deal with people we can’t. Choosing to instead assess whether the demands themselves make sense or not is much more risky than just doing the prep, especially when the person setting such expectations has power over your future.

Now, the conventional advice we read about in countless management articles and books is to “manage up.” Make your boss’s job easier; clarify their expectations and help them understand why they don’t need as much as they think they do. And have a candid conversation about how these reviews could work better.

At times, these ideas help. But to be perfectly honest, as someone who worked in these rooms and coaches hundreds of leaders in them now, I can say that the theory sounds better than the practice.

There simply are rooms where asking for more autonomy is interpreted as resisting oversight, and admitting that the workload is unsustainable raises questions about your ability to handle it. The coach or thought leader giving the advice to manage up doesn’t have to live with that boss afterward. You do.

So what is available to you when the demands are unlikely to change?

Both my clients were beginning to separate what their boards and bosses expected from what they believed those expectations proved about them.

For instance, they recognized that there is a difference between “My boss expects me to know this” and “A competent person in my position would already know this.”

Because when you depend on someone’s approval, those statements can start to sound identical. Instead, it takes discerning judgment to separate them.

Of course, some questions will expose gaps you need to address. But others reflect a level of detail that this particular person expects, whether or not it improves the decision.

And you may have to supply the detail either way. But you can also do that without accepting every expectation as a reasonable measure of your competence.

Going forward, consider trying a brief assessment after your next difficult meeting, before the familiar self-criticism takes over. Ask yourself:

What did you actually miss?

What couldn’t reasonably have been known?

What remains uncertain because it is uncertain, regardless of how hard you could have prepared?

Reflecting on these questions may make you feel less pressured to prepare, but they can perhaps keep you from wasting an evening questioning your ability.

If you choose to stay with a work situation like the above, know that it may be impossible to make your boss or other senior stakeholders easier to engage; but you can keep reminding yourself that what they need to hear to feel satisfied isn’t always about you or what you can offer.

Instead, it is a habit that they need to manage. Maybe over time, as you worry less about pleasing them, they may even come to the awareness that their over-reliance on information is stunting their strategic altitude as well.

In the meantime, do your best to prepare for that next meeting. But you don’t have to spend tonight putting yourself on trial for the past ones.

The threshold question

Where do you allow someone else’s expectations to make you believe you’re not doing enough?

Until next week,

Nihar

Nihar Chhaya coaches senior leaders on navigating the transitions that come with business, leadership and personal success. 

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