Your 3 step plan to help navigate your nonprofit leadership challenge

Kathy Archer
4 min readSep 12, 2022


Jennifer recently came to a coaching call infuriated with her boss. Jennifer was a middle manager and found herself entangled in a triangle of sorts with her boss, herself and her team.

Often her boss would undermine Jennifer in meetings. Without knowing all the facts, he would make a decision and announce it before conferring with Jennifer.

By the time we got onto our coaching call, the above scenario had happened numerous times. Jennifer noticed how it triggered her anger and prompted ineffectiveness in the team. The team didn’t know whom to believe anymore. It was all a big mess, and Jennifer felt undervalued and unsupported. However, Jennifer hadn’t had the courage or understanding of how to address the issue with her boss. Therefore, she’d been avoiding it.

Have you ever avoided a tough conversation?
We have all done it, but avoiding tough conversations does not resolve them. On the contrary, it only worsens them and often leads to deteriorating your team’s effectiveness. Jennifer had realized that. It was why she’d brought the issue as a topic for our coaching call.

Jennifer started with why it was important to figure out
Through coaching, Jennifer was able to get reconnected to why she needed to engage in this potentially intimidating conversation with her boss. She was passionate about her staff members being supported and wanted them to have solid supervision. In the end, addressing the conflict with her boss would be better for her and her team. Even though it would be difficult, it was worth figuring out.

Take the first step to resolve the issue
Jennifer realized that in a “perfect” situation, her boss would recognize incongruences in messaging and deal with them himself. However, life isn’t perfect. Jennifer knew she needed to be the one to tackle the problem head-on. She did just that. Jennifer took the first step and arranged a time to meet with her boss and then shared her concerns.

The result isn’t always perfect, but it’s a movement forward
Now, of course (remember, this isn’t a perfect world), he didn’t quite see the story like Jennifer. He did, though, become more aware of checking with Jennifer before he issued new standards of practice. As a result, Jennifer felt more confident and sure of herself. By stepping into the difficult conversation, Jennifer discovered she could fight her own battles rather than hoping they would magically disappear.

What is the tough conversation you need to have?
Perhaps you’ve found yourself in a similar situation, sandwiched between frontline staff and management. Other times you may have found it is the supervisor who isn’t dealing with their team, and you see the mistakes happening. In that place, the tough conversation needs to happen with your subordinate, encouraging them to handle their reports more effectively. It could also be peer-to-peer where your co-worker is stirring the pot, causing havoc on the team.

When you realize a storm is brewing and know it’s not going away, it is probably time to wrestle the tough conversation yourself. Below find the steps that will assist you in moving through the challenge.

Your 3 step plan to help navigate your nonprofit leadership challenge

1) Identify the issue
Notice that you may have been avoiding or hiding from the issue. Perhaps you push it away, praying someone else will deal with it. You’ve probably noticed, unresolved, that the issues continue to rise again and again. Each time you become aware of it, you probably tense up, get a knot in your stomach or feel anxious. By noticing when something is off, you help identify the problem that needs to be dealt with clearly.

Jennifer recognized the challenge was when her boss skipped over her role and function and did her job. She would have preferred that here and her boss discuss the issue before communicating them to the team. But instead, she identified the problem as feeling undermined.

This step is about getting clear on what precisely your challenge is so that you can communicate it.

2) Take responsibility for moving things forward
Stop pushing the problem away and blaming others for not fixing them. Instead, recognize that it is your job as a leader to resolve the issue. No, it may not be your problem but acknowledge that it is your responsibility to lead your team into a more effective, cohesive working environment.

That may mean that you need to be the one that grabs the bull by the horns. Jennifer did just this when she initiated a conversation with her boss.

3) Create your plan for dealing with the challenge
When you realize the problem is not going to go away and no one else will deal with it, it’s time for you to address it. The best way to move through the muck is to be clear about what you will do it.

  • Set a time that you will have this conversation
  • Review any communication training that will help you
  • Write out the key points, including the sentence you want to begin with
  • Identify anything you need to do before the conversation to ensure you will be composed and confident

Dealing with challenging exchanges is not always easy but worth it
Even though they are tough, I encourage you to take the initiative to have tough conversations. You will find your confidence and courage increase the more often you tackle them. As a result, your team will be more effective, and you will also discover that you can enjoy your work more.

If you need more help planning for your tough conversation, try this.

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Kathy Archer

Helping women leaders make it in the nonprofit world. Leadership Development Coach * Best-Selling Author * Wife * Mom * Grandma * Mom to one boxer named Zeus!