How Do I Approach a “Headstrong” Leader?

Dear W.H.,

It’s interesting. In many cases we can’t understand why someone who seemingly wants to retire wouldn’t do everything in their power to just set the wheels in motion and get it done. However, in many, many cases the person’s career is their identity.

Advisors, in particular, are often entrepreneurial business owners. They started from scratch, have built a successful practice, and have clients who trust and turn to them for answers. Moreover, most advisors enjoy what they do. Walking away from it and figuring out what’s next can feel like a daunting proposition.

I was recently in a client office that is undergoing a client transition process. The two senior advisors aren’t going anywhere; they will stay with the practice and continue to lead and contribute to the success. However, I asked each one separately, “What’s next for you once all of the clients are transitioned?”

Neither of them could answer the question. It’s a natural human reaction when we’re not sure what’s coming next that we hold on to whatever we have now and stay put! This is why inertia is often the biggest competitor when you are trying to get someone to make a decision or a change.

That said, of course, over time things do change, and even must change. In this case, you have someone who is likely uncomfortable with being pinned down to dates and steps. Many successful entrepreneurs are not process people. They want to keep things open and be able to change their minds as new information comes along. This doesn’t mean he has no confidence in you or doesn’t trust you – it means he is not someone who is going to lean into a plan of action very easily.

Your only option in a case like this is to have a frank conversation about your expectations, your needs and your frustrations to date. You don’t want to threaten and tell him you are considering whether you should stay or go. But you do want to articulate your hope there would be some clarity around when he wants to engage more fully in the process of transition.

It’s not really your role to help him think about his next steps, but it may be in your best interest to do so. Perhaps you could ask him what he sees for himself in six months, one year or five years. You might gain some insight into what he is thinking (or possibly afraid of). It’s a similar conversation to one you might have with a client, so turn those excellent skills of consultative questioning on him. See if you can’t get him to uncover his own thoughts and feelings about what he needs to do next.

I never tell people to stay or go in any situation. That being said, if you take the steps to engage with him differently and don’t get good answers, then you need to make a decision for your own career.

Dear Bev,

When I use the word “headstrong” I am not exaggerating the style of the senior advisor in our office. She is a bulldog, and has been extremely successful as a result. However, when we, the team members, want to raise a question, a concern, or an issue, she shuts us down so quickly it’s like we had never spoken. How do you get someone to listen who doesn’t want to do so and doesn’t think they need to? We’re constantly strategizing on how to present ideas or information, and as soon as we try and present or suggest, she will respond with “I don’t have time for problems – solve them yourselves.”

Anonymous

Dear Colleague,

If I had the answer to how you get someone to listen who really doesn’t want to do so… I’d be a very wealthy woman. People would come from all over the world to use my services! You have a situation here with someone who likely doesn’t enjoy dealing with details, doesn’t believe she should be the one to fix everything and might even be a bit afraid of what you are bringing to her and why. She could interpret it as complaining about how she is running things and her performance as a leader.

When I teach graduate classes in leadership, so much of the focus is on honing one’s EQ and being an active and engaged listener. It is truly hard to gain credibility and lead effectively when you don’t see how you are shutting people down and you fail to open yourself up to new learnings and ideas. It is the essence of great leaders to listen to and care about what their team members have to say.

There are only a couple of workable options in a situation like you have here. You can’t tell someone like this she isn’t listening or that you feel shut down when you speak with her. That will only lead to defensiveness. She may even accuse you and/or your colleagues for either not being great communicators or not understanding your role as that of solving problems for her rather than bringing them to her.

If there is anyone on the team who has her ear and whom she trusts, you might ask that person to have a candid one-on-one conversation with her separately. They can share that there could be things she is missing that would be important for her to know in her role. Perhaps having one person she trusts speak with her, rather than a number of people on the team, would allow her to listen differently.

You could try asking whether the team could run some sort of behavioral profiles and do a team meeting to review them. I’ve often found, in my firm, this helps leaders to see more objectively where they are strong in their communication style and where they need work. We prefer the DISC and Driving Forces profile (with EQ) but there are many others on the market such as Meyers-Briggs, Strengthfinders, Insights and so on. If you get someone qualified to have a discussion with the whole team, they might help her see how she comes across to others.

I am a fan of something called “Obstacles Meetings.” Here team members have a chance to share an obstacle they are dealing with and discuss whether they can control it, influence it or neither (as in, it is out of their control entirely). You could suggest to her the team comes together once per month to do this. Somehow obstacles can be easier to understand than issues, problems or challenges. The last three can sometimes be construed as negative concepts.

When all else fails, you could try bringing the team together without her and solving as much as you are able to without her involvement. I realize in many cases as the boss, she would have final say. However, it can be therapeutic to focus on what you can control and solve for it. It may take your attention away from your frustration in not getting anywhere with your boss!

Beverly Flaxington co-founded The Collaborative, a consulting firm devoted to business building for the financial services industry, in 1995. The firm also founded and manages the Advisors Sales Academy. The firm has won the Wealthbriefing WealthTech award for Best Training Solution for 2022, 2023 and 2024. Beverly is currently an adjunct professor at Suffolk University teaching undergraduate and graduate students Entrepreneurship and Leading Teams. She is a Certified Professional Behavioral Analyst (CPBA) and Certified Professional Values Analyst (CPVA).

She has spent over 25 years in the investment industry and has been featured in Selling Power Magazine and quoted in hundreds of media outlets, including The Wall Street Journal, MSNBC.com, Investment News and Solutions Magazine for the FPA. She speaks frequently at investment industry conferences and is a speaker for the CFA Institute.

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