“Coach Up” to Hold Your Boss Accountable to Promises

Lara Frankovitch
The Startup
Published in
4 min readJul 25, 2020
Photo: seventyfour / Adobe Stock

Ever had the feeling of an empty promise at work? The thing that comes up every once in a while but never seems to happen?

Maybe it is the promise of a new project, a new working arrangement, a raise, or a promotion.

After waiting 3 months for a promised promotion, one of my coaching clients was frustrated. She didn’t want to ruin her chances of getting promoted appearing pushy, but she was quickly losing trust in her boss’s ability to deliver on his promise.

I taught her to “coach up.”

Coaching is the art of asking thought-provoking questions and holding the other person accountable, and it is especially effective to help a boss follow through on their promises.

Here is the step-by-step plan my client used to “coach up.”

Get the topic back on the table

Maybe you’ve avoided the topic lately with your boss, but it is time to get it back on the table for discussion!

“We haven’t chatted about XYZ in a while, but it is still on my mind.”

Even though it hasn’t left your mind, there is a chance your boss has forgotten about the promise, especially if they made it in passing.

Clarify your understanding

Having a clear understanding of the promise is critical to driving it forward.

In the case of a promotion, it could have strings attached to things that you need to do before your boss can fulfill the promise (achieving a particular metric, finishing a certain project).

To get clarity, say, “Hey, we’ve talked about a potential promotion for me, but I want to make sure I clearly understand. Here is what I think… What am I missing?”

Ask the 4 magic questions

Magic coaching questions are open-ended (can’t be answered with yes or no) and illuminating. They move the conversation forward.

Here are the 4 magic questions to ask when coaching up to hold your boss accountable for a promise:

  1. “What are the 3 main things that need to happen?” This question gives you a better understanding of the process.
  2. “How can I best support you in this?” Asking this question shows your boss that you are on the same side, and you both have a role in making this happen.
  3. “What are the potential roadblocks?” Understanding what might get in the way gives you better insight into the chances of the promise actually happening. More importantly, asking the question forces your boss to think about potential risks. This will hopefully drive action on their part to mitigate the risks.
  4. “What would be a good date for me to check in again?” This permits you to broach the conversation again. Asking for a specific date causes people to feel more accountable.

Write it down

Writing down conversations brings a level of seriousness and commitment that verbal conversations often lack.

Document the answers to the magic questions while you are having the conversation. If you wait until the meeting ends, you might have a hard time recalling the details.

Feel free to mention you are taking notes. It gently hints to your boss that this conversation is important to you.

After the meeting, clean up your notes and send them to your boss over email. It doesn’t hurt to say thanks for the conversation and that you want to confirm you understood everything correctly.

You should also add a reminder on your calendar about a week before the date you agreed to check-in.

Follow up

About a week before the date you agreed to follow up, you should give your boss a head’s up that you’d like to check in on the conversation.

Say something like: “When we last chatted about XYZ, you mentioned that x date would be a good time to follow up. I’d love to cover this first in our next 1:1.”

Likely, your boss has a full plate, and giving warning that you want to talk about it will give them a chance to make last-minute progress, hopefully leading to a more fruitful update, and ideally, the fulfilled promise.

If your boss hasn’t made progress, try these approaches:

Drive to more clarity: “We’ve been discussing xyz since April, and I feel I’ve done the things we agreed I needed to do for this to happen. Can we revise what needs to be done to move forward?”

Be clear about the impact to you: “To be completely candid, I’m feeling disappointed that xyz hasn’t happened yet. I’ve completed all the steps we talked about.”

Ask for advice: “What would you do if you were me in this situation and waiting for xyz to happen? How should I be thinking about this experience?”

If your boss still doesn’t follow through with the promise, it is probably time to look for a new boss.

Use this “coaching up” tactic to drive accountability the next time your boss makes a promise. Even if coaching up does not get you the outcome you were looking for, it is a good exercise to strengthen communication with your boss.

Want to talk more about leadership? You’ll leave a 30-minute complimentary session with me with actionable next steps about a business issue keeping you up at night.

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