Six Helpful Strategies for People Working with Difficult Leaders

Suzanne S. Davenport
6 min readSep 6, 2023

If you live long enough, you will likely have to work with difficult leaders or just difficult people. And by using the term work in this context, I simply mean that you will have to communicate with them. It could be a family matter, neighborhood dispute, or an office conflict that needs to be resolved. Some people can just be difficult. And so, I’ll offer six strategies to help you work with difficult leaders.

In my experience, working with difficult leaders can quickly drain the energy out of an organization or a team. And since I’m always trying to help teams improve their effectiveness, it’s important to develop good coping strategies when you must work with difficult leaders.

Begin by accepting that the only person you can change is the one in the mirror. And then, only you can assess whether you want to spend half of your waking hours working in that organization. On the assumption that you plan to continue doing that, here are some helpful strategies.

1. Practice meditation and journaling

If you don’t have a meditation practice, I recommend you download a mobile app to guide you in starting one. I use Headspace and love it. I frequently skip using the app but I’m pretty good about tying in my meditation practice with my spiritual discipline, exercise, daily journaling, and planning efforts. And, I step up the app use when a client, friend, or family member starts to stress me out. I also find that journaling about the thoughts that keep interfering with my meditation practice is helpful.

Only you can decide what practices are important to you, but I suggest you begin with the question: Am I happy with letting others control my life, or do I want to take control of my days? If you want to take charge of your destiny, then you need to learn how to calm your brain. Even if you have ADHD, you can work on this. It may be harder for you but there are experts who can help you assess whether you should be on medication, and which kind.

A steady meditation and journaling practice will help you work with difficult leaders.

2. Align with others who are focused on the same goals

I remember working with a company some years back, and the owner qualified as a difficult leader — by anyone’s definition. She was kind and lovely, but difficult. One reason was that her brain was always on — and always cogitating on new ideas to save the company. That’s not a bad thing. But it made executing quite challenging as we never knew when the goal line was going to be moved. And we never knew when she might blow up at us.

One strategy that seemed to help was to align with the others in the organization and how we would respond to her. We challenged her in one of our morning meetings to better articulate her goals so that even when an activity scope was changing, we could ask ourselves and then her, how the new activity scope aligned with the project itself, and her formerly articulated goals.

We all found it helpful to have documented our understanding of what the goals, projects, and activities were. And when scopes and projects were evolving too fast for us, we could redirect our attention to the board where all of this was documented with sticky notes. We could frequently add a new sticky note to the backlog without redirecting current work. And we could help her understand that if we changed our execution strategy too fast, we wouldn’t deliver anything on the next due date.

3. Get to know the difficult leaders as people

One of the reasons that I enjoyed working with this particular woman is that I liked her personally. We shared a lot of common beliefs and she was simply a brilliant woman. Sometimes brilliance can make people harder to work with. But it’s hard to not like someone just because they are brilliant.

In getting to know this leader, you can learn why they are difficult. Is this someone with a mental health issue that makes them prone to rage? Is the difficulty new, and could it be explained by a change in their health situation? In either of those situations and depending on your organization and how comfortable you have become with this person, you may need to consult HR for help. Or you may prefer a drink after work or a walk to calmly inquire if something is going on that is causing these outbursts.

Is it someone who is just a go-getter and upsets others with an aggressive, bullish style? If that fits, maybe you can confront him or her with a humorous question — such as, do you think we could bring a sprinkler to this problem instead of a firehose?

If getting to know a person is hard to do, you may ask yourself if you have difficulties that are contributing to the problem. Do you bring ultra conservative or liberal beliefs about controversial topics to the workplace and inflict them on others? Sometimes, we must learn to set aside our own personal beliefs about non-work matters and focus on the job that we are being paid to do.

You don’t have to be best friends with the people you work with, but you must demonstrate respect for everyone.

You don’t have to be best friends with the people you work with, but demonstrate respect for everyone. #respect #empathy #leadership #teamwork #projectmanagement #business #smartprojex

4. Don’t be afraid of difficult conversations

When I work with younger people, particularly people who are doing junior work with senior people, I find that some young people are afraid to confront more senior people. It’s understandable. Many were raised to respect their elders. And yet, once a person goes to work in a business, everyone needs to understand that we all have a value to bring to the table.

Doctors prefer practicing medicine, over filling out forms. A young person, working in an administrative role, might see efficiencies that can be improved. The newly hired lawyers might have technology gifts that are very valuable to more senior lawyers who aren’t keeping up with every new technology announcement. Not only do we need to encourage respectful relations between employees, but we need to encourage younger people to speak up if they seem reticent. We can all learn from each other. But we may have to have difficult conversations to move forward.

When we work with people in other cultures, there will be language nuances that can trip up anyone. I remember when my husband was deposing a senior executive in a German company and noted at some point that the executive’s strategy was quite shrewd, thinking that shrewdness might be a very smart strategy. The witness did NOT see that as a complement, and it slowed down progress.

You might find that the difficult conversations, if you are willing to have them, will open the door to better understandings with difficult leaders.

Don’t be afraid of difficult conversations. You might find that the difficult conversations, if you are willing to have them, will open the door to better understandings. #talk #conversation #leadership #teamwork #business #smartprojex

5. Be quick to apologize and forgive

We are humans and we aren’t perfect. We say the wrong things, get hurt, or insulted. And we get into debates and disagreements. That is life and business. But we must have the hard conversations to make progress. And smart people are going to disagree with each other sometimes. And that is good. We should encourage that. And we should encourage apologies and forgiveness.

6. Keep good records in a safe, secure place

Sometimes, it will become apparent that someone needs professional help, or the services of HR, or perhaps even dismissal. It is critical that there be documentation to support a dismissal. So, document conversations, expectations, results, and concerns in a safe, secure place. The top of your desk is not a great place. And email may not be appropriate. Get advice from professionals.

Good luck when difficult leaders are owners. Sometimes there aren’t easy answers or solutions. And you will just have to weigh the benefits of the job against the stress of working there. But try having the difficult conversations, aligning your efforts with others around you, getting to know everyone on the team, and being quick to apologize and forgive. And learn all you can about leading others and managing projects. If you are looking for a book, try Herding Smart Cats: Project Management Reimagined.



Suzanne S. Davenport

Writes on project management, leadership and reimagining work. Author: Herding Smart Cats.