Leading the Leader: How To Hold Your Boss Accountable

Have you had a boss who frustrates you? Likely, the answer is yes. If you've ever worked for a manager who won’t stick up for you in meetings, or who seems to be a pushover when they really need to stand firm on a subject matter, or you've worked for a boss who says one thing to their team but does another when with their peers.... this post is for you.

I've been in your shoes. I've been in the place where I needed my boss to show his/her influence because their influence was simply beyond what I could do in my current role. I've been in the situation where I needed my boss to step up their game and truly lead our high-performing team. I've had experience navigating the murky waters of hard conversations and seen incredible results. Here are a few things you can implement today to move the needle toward productive and positive change:

Prepare for a hard conversation

Starting is the hardest part and my advice to you is to simply, just do it. Remember that it will be messy. It will be uncomfortable and awkward. Be open about that - being honest with your boss that you feel awkward and a little nervous about this discussion, sets the tone that you are moving out of your comfort zone and that this is really important. At the end of the day, just remember that you and your boss are working toward the same goal. If all else fails, go back to that main point!

Remove your assumptions & get curious

Remember that your boss may have their own story…get curious and double check your interpretation of what you think you know. You may not have all of the facts.

Here are some questions that lead to productive conversation rather than making others feel defensive, and save you from making assumptions that aren’t necessarily correct:

  • How did the conversation about __________________ go?

  • What happened with the ____________ situation?

  • What’s the next step regarding __________________ ?

  • How can I help you be successful so that we achieve __________________ ?

Leaning into curiosity is the best way to build a bridge between frustration and understanding. It's a space of grace and authenticity; a great default posture for any leader.

Do the hard thing

There's no other way around it; you must have heartfelt crunchy conversation with your boss. Schedule a one-on-one and ask for some time, and do it when you know you can have their full attention (read: not before a board meeting, for example).

In this conversation, challenge yourself to be courageous and have an honest and vulnerable conversation about what you need to be successful. Be clear with your boss about how they can support you to be successful.

Here's a leadership guru tip:

Start the conversation off on a positive note. Remind your boss what you appreciate and enjoy about working with them. There is power in affirming someone's qualities and strengths.

Be prepared to ask for what you need (and be specific)

You need something different from your boss. In order to do your best work you need the following to happen:




You need your boss to do the following actions in order to achieve your goal:




Follow up and schedule time to review action items

Remember that this is an iterative interaction. Oftentimes there needs to be multiple versions of the conversation to truly shift behaviors and the progression of the objective or the relationship. Learn to get comfortable with being uncomfortable: ask for what you need, do the hard thing, follow up and hold others accountable who may be having a hard time doing it for themselves.

If crunchy conversations make you queasy, or you'd like a pep talk to prep for one that you're planning to have, reach out to me today and schedule your complimentary coaching session!

In Service To Your Greatness,


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