This week’s method: The Follow-Through Test
Stop rewriting that email. A simple test shows whether your boss is changing, or only you are.

Everyone in organizational life has a boss (or someone with more power whose expectations they need to meet). Even the CEO answers to a board and chairperson on much of their work.

In most settings, a more co-creative relationship with our superiors, rather than one of deferential subservience, leads to better results. Collaboration improves, and the team’s talents are put to better use. So, influencing bosses by “managing up” is a skill many leaders must learn, in the same way they learn to manage down.

Now when you’ve worked hard at managing up, you may have found yourself trying a lot of different approaches just to see what sticks.

Perhaps you’ve rewritten an important email to your boss as many as four times:

The first attempt sounded frustrated. Then your second one sounded unsure. The third became so careful it barely said anything. And finally, the fourth was short and kind, offering a solution before they had to ask.

Maybe the last one was the right one to send…or in retrospect, maybe it shouldn’t have been an email at all.

Honestly, how long will you keep guessing and revising in your relationship with them?

Much of the advice about managing up assumes there is a workable arrangement waiting to be found: give them clear reasons to do something, appeal to shared goals, ask for input, and so on. And sure, these steps can work well.

But what this conventional advice can’t do is give you some magical control over another person’s willingness to share power or keep an agreement.

We need a better way to gauge how much “managing up” is actually worth trying.

The cost of trying too hard

I’ve worked for bosses who understood exactly what I was asking for and still refused to budge.

You may have worked for a boss or a board that wants your honest opinion, just as long as it doesn’t challenge their judgment.

And there are always people in authority who know they gain more from your availability and helpfulness, so they are reluctant to respect any boundaries you try to set. They see your availability as a privilege of their position, so why wouldn’t they make the most of it?

Let’s face it: bosses are entitled to get the most from the people who report to them. That isn’t the problem.

The real issue is how common it is for conscientious people to get stuck trying to manage these bosses, believing there has to be a way to change them. And that if they just try a bit harder, they’ll be the one to finally crack the code with that particular colleague.

To their credit, because they are conscientious and often introspective, the most talented leaders will take the well-worn advice to “Be the change they want to see in others.” So, they will question themselves before expecting their boss to change, asking:

“Could I have been less defensive? Could I be more strategic going forward? Should I get better at making them feel included? Have I really tried everything?”

This kind of reflection is absolutely worth it as a first step. But with some bosses, your heightened self-awareness and personal adjustments still won’t guarantee they will adjust in return.

And when relied on too long, self-reflection without any movement from the other person has a real cost: something I call ruinous rumination.

You start spending more time preparing for your boss’s reaction than thinking about the work. You leave meetings replaying your tone in your head, instead of asking whether your request got a fair answer. In essence, you get better and better at accommodating a situation that never changes.

For a high achiever, thinking hard about work after hours is part of what makes you successful. You ponder new ways to solve problems, and that’s why you excel.

But research shows that overthinking about negative emotions and distress at work (also called “affective rumination”) is a clear predictor of rising exhaustion.

Replaying the problem with your boss in your mind over and over is not only unproductive for your shared goals with them, it wears you down and weakens your stamina for sustained effectiveness.

So, given the clear limits of managing up, it’s worth asking a different question:

What evidence would tell me this relationship is becoming more workable?

Here’s a method my clients have used when managing a boss that seems resistant to finding agreeable and consistent ways of working together.

The Follow-Through Test

1. Pick one decision and agree on its limits.
Choose something specific you want to own, such as a vendor choice or a hiring call, instead of a general wish for “more trust.” Agree on the boundaries and on when you’ll update your boss. Then confirm in a short note: “I’ll make the vendor decision and update you Friday.”

2. Decide now what you’ll do if the agreement doesn’t hold.
Write your decision as an if-then plan for yourself: “If this decision is reversed without discussion twice in the next month, I’ll ask once what changed. Then I’ll choose my next step.” Deciding this before you’re frustrated lets you respond consistently and in line with your values.

3. Watch for a few weeks and write down what happened.
Record whether the agreement held, using plain facts rather than how the meeting felt. Remember that one conversation tells you little; relationships ebb and flow, so look for trends in their behavior, not just the first time they let you down.

If the agreement holds, you may find the relationship is better than you feared.

If it doesn’t, you now have useful data. You can clarify what happened and give the arrangement one more fair chance. Or you can choose not to.

What you don’t have to do is keep questioning whether you should have worded something better or spoken in a different tone.

After trying The Follow-Through Test, you might find your boss can offer less freedom than you want, but enough to make the role worthwhile. And based on that information, you might narrow your commitments, find support from another trusted leader, or explore a different role.

Or you might accept the situation for now because the income and opportunity are worth it.

Whatever you decide, hopefully you’ll have more peace of mind, because you’re no longer spending all your energy looking for the “perfect” way to reach and change someone else.

If you don’t feel at peace, just know that this is often the toughest threshold for the skilled, successful achiever: being okay with not trying harder.

You may have to loosen your hold on being the person who can make any relationship work. Just know that in the long run, being comfortable with doing less will help you see what your effort is producing and what it isn’t, so you can ultimately decide how much more of yourself to invest.

This week

• Write one sentence describing something that keeps happening with your boss (that you’ve been treating as a problem) and how you explain yourself.

• Pick one decision you want to own and send a short note confirming the limits and when you’ll update them.

• Write your if-then plan and keep it somewhere private.

• Put a date on your calendar, three or four weeks out, to review what actually happened.

• Limit yourself to one draft of the next message to your boss, then send it.

• Tell one trusted person what you’re testing, so you aren’t carrying it alone.

Feel free to let me know how this works for you. I read every reply.

Until next week,

Nihar

P.S. Are you, or someone you know, moving into a bigger role?

I've written a free guide about the five changes executives scaling up often don't anticipate.

Free download: What Changes When The Role Gets Bigger

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Nihar Chhaya is a trusted coach to CEOs and senior executives at over 40 of the world’s top companies including American Airlines, Coca-Cola, Cox Enterprises, Lockheed Martin, DraftKings and others.

A Master Certified Coach (MCC) recognized by the International Coach Federation, Nihar helps leaders navigate transitions, lead more strategically, strengthen their influence, and build trust across their teams.