Tim Wolfred: What I Learned from My Executive Transition

Tim Wolfred

For eleven years, I led CompassPoint’s Executive Transition (ET) program, helping organizations and leaders to plan and execute effective leadership transitions. In 2010, I participated in one of the toughest transitions I have ever worked on: my own. While I wasn’t the Executive Director (ED) or CEO of CompassPoint, I was a long-time senior manager, so my situation has some parallels to an ED departure. Did I learn anything new from my own transition process? Did I practice what I preach to organizations and leaders about transition planning? Yes and yes, and here’s my story.

I had been thinking about transition for three years before I left – a very common occurrence with longer serving leaders. I knew succession planning was a good practice, so 18 months before I left I started doing some succession planning on my own. I started backing up everything I did, making sure I lined up someone to carry on my duties – for instance, I connected another staff member to the two major, longstanding funders I worked with so there would be some continuity and I made sure my work files were in order and organized.

Then about four months before making my final decision, I engaged a coach (all on my own personal time and funds). This was probably the most significant and useful thing I did. My coach helped me talk through and figure out what I really wanted to do with the rest of my life. I had reached age 65 at that point and the urge to make a change had been growing, but what change and how to do it were the big questions. One option would be to stay on staff but cut back hours. Option two would be to make a clean break and move to another country. I landed on a third option between the others: to leave my staff position and set up an independent consulting practice. Once my decision was made I talked it through with CompassPoint’s CEO Jeanne Bell (my coach helped me process the steps to do this in the right way, too).

Applying our model

Modeling good consulting practices, I followed CompassPoint’s Executive Transitions model in my own transition. Here’s what I experienced living out some of the key components:

  • Getting a coach - After having preached coaching for so long to clients, my own process gave me much appreciation of the value of coaching.
  • Succession planning – I made sure there was a back up for me within the organization, another person who knew the background, history, and planned path for the program. Shared leadership like this and strategic leader development are good practices regardless of when a departure is intended. It’s a good risk management practice.
  • Letting go rituals – The goodbye party CompassPoint held for me was extremely helpful. It tangibly marked the end to my full-time staff status within the organization. I liked the scrap book people put together and the other rituals of appreciation. I also made a point to go to lunch with the external partners I had worked most closely with.
  • Defining a future role with the organization – Many executives want to stay on in some capacity after leaving the ED role, and getting that role clearly defined is very important. Though I was a senior manager not an ED, I also had the desire to keep an ongoing connection. I worked closely with the CompassPoint Management Team to clearly define a new role for as a Senior Affiliate. It’s a relationship that serves CompassPoint and me.

Surprises along the way

I was surprised by how emotional this process was. It increased my empathy for what executives go through on the emotional side of this change and in letting go. As a result I’ve started to focus even more attention in my ET work to the personal challenges experienced by leaders as they leave their job.

Similarly, I’ve always viewed coaching as very valuable, but in practice, its impact on my own planning and thought processes were huge.

What I would change about my transition

I would change nothing about the transition and succession model. As a practical matter for someone going out on my own as a consultant, however, I would have paid more attention in hindsight to developing my own skills with technology. I had it easy as a staff member with so much IT support around me. After I left I had to handle this all myself. Maybe this is generational; regardless, I think it’s important to build up this skill if you need to.

Change is good…eventually

I’m feeling really good right now. I’m able to focus on the things I want to focus on: the client work. I have more control over my schedule. It has worked well in that way. And I’m still connected to CompassPoint and I still enjoy the camaraderie with my colleagues on staff, working on projects together.

But I admit there are things I miss. What I miss most is daily contact with bright, energetic peers (and, again, the IT support). As a staff member I encountered a great variety of folks on a day-to-day basis. To address this people connection (or, rather, disconnection), I’ve joined a peer group made up of members who do Executive Transitions work around the country. I’m putting more energy in this group and starting to “find” myself in the activities we’re doing.

It took about 4-5 months to transition out of CompassPoint – both mentally and in my workload – and I’m happy to say the results match what I planned. But it wasn’t easy. It’s a testament to good preparation and the goodwill and support of the people at CompassPoint, starting at the top with CEO Jeanne Bell.

By Tim Wolfred (Tim@WolfredConsulting.com, 415-647-5265) / January 25

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