Leadership Check-in: A Case Study

Explain in your own words the work you did with Jennifer.

Jennifer has been my coach for a number of years, helping me build my self-awareness and improve my leadership performance as my company scales. I’m moving away from being the head of a business to a leader, which requires different skills.

In one of our coaching sessions, we talked about my relationship with my team and who I was as their leader.

I realised I didn’t have any feedback - objective data - about my leadership. My analysis was based on guesswork about how I was perceived.

I was looking for unfiltered honesty, clarity, and greater awareness of any blind spots.

What prompted you to embark on this work?

I have a brilliant team around me and regularly ask for feedback, as I want to be a better leader, the leader they need. I often wondered how much people were telling me and what was left unsaid.

One of my challenges was that my team are, first and foremost, my friends. Having frank and honest conversations about performance can be difficult. This realisation instigated our 360-review.

What did the Leadership Check-in involve?

From scoping the questions to producing and debriefing the report, the whole process took around six weeks to complete.

Jennifer helped me to choose people who would give perspective on who I was as a leader. She was very clever in doing that, in that she didn’t only consider my immediate team. She also wanted to speak to two people I'd worked with previously and my husband, who sees me in a totally different light! 

Once I’d made the introductions to the people I wanted her to interview, Jennifer managed the whole thing.

She had conversations with each of them and wrote a highly detailed report, which we explored fully in a coaching session. 

The hardest part of doing this kind of work (as a coach) is making sense of the notes you've scribbled down. She organised the information into thematic questions and made real sense of what had been said. She gave it structure and order, and it was a pleasure to read.

What was the most valuable aspect of your work together?

It’s rare, as a leader, to hear what people really think, and that's what the leadership check-in gives you. It’s gold dust. 

Several things spring to mind as most valuable:

Objective data to identify and understand blind spots and strengths

Jennifer really helped me to understand my blind spots and strengths. Giving my team the space to have an honest, frank, and anonymous conversation with a coach who could probe their perceptions was a powerful experience.

It’s very different to asking people to give feedback online. If you ask someone to fill out a form, they will tell you very different things than if you were being interviewed. 

If a highly experienced coach is interviewing you, they’re going to dig deeper using all their coaching skills. That’s exactly what Jennifer did to get to the nub of the team’s feedback and really understand it. 

Fresh and novel perspectives

I would never have thought to talk to people outside of my business in this exercise. Challenging me to ask for and analyse their perspectives was probably the most valuable thing of all. It gave me a different view of what my strengths are from people who had seen me operating in a completely different role. This, in particular, boosted my confidence and helped me to remember core capabilities I had taken for granted or archived in the back of my mind.

Realising what I took for granted

I know where we’re going as a business, and I thought everyone else knew too. The feedback from the team suggested otherwise. I’m now being intentionally clearer in my communication around my vision for the business, so everyone is guided by that North Star and knows our planned route to get there.

Our detailed debrief

Our debrief session addressed questions and concerns and put the feedback into context, which was extremely helpful. Jennifer brought the data from the report to life for me and helped me see what was said in the context of her other conversations collectively.

Jennifer told me the absolute truth, but she was there with me, absorbing, processing and making sense of the feedback to feed directly into my development roadmap.

We regularly refer back to that report - it’s a crucial resource now.

What changes have you recognised as a result of this work? 

It was a nerve-wracking experience and one that was difficult to press the button on. It requires you to be vulnerable and brave and hear things you might not want to! But that’s only a good thing. As I say to my clients all the time, awareness is the first step toward change. Acceptance is the second.

The biggest change has been in my confidence in myself and my decision-making. There was a lot of positive feedback that I hadn’t fully appreciated, acknowledged, or absorbed up until that point.

Certain phrases within the report have stayed with me. I refer back to them and repeat them to myself when I face a challenge. These include the desire for my team to see me “step up” more and own my role as a leader. I also valued the reflection that some of my team were friends first before they became employees. Because of this, I will always need to be sensitive but bold when asking for what I want or pushing back.

It reassured me that, although there’s always more to learn, I have everything I need within me to be the leader I want to be. 

Going through this process with my team, and specifically sharing the report with them has brought us closer. The knowledge that I’m working on myself based on their experiences has built trust between us.

It reinforced our culture of openness and honesty as it invites constructive challenge. The check-in gave them explicit permission to continue bringing feedback and to challenge me when I need it.

What’s happened since? What are your next steps?

I found working through Jennifer’s detailed report so valuable I wanted to do something similar with my whole team. I shared her report with them, and as an add-on activity, we held a whole leadership away day at The Shard, expertly facilitated by Jennifer.

Having done the 360 analysis with the team as part of her report, Jennifer was well-placed to facilitate our away day offsite. The team knew her already, and she understood our dynamics. She had their trust, so they could be vulnerable from the outset.

On our away day, we explored:

• What we wanted to do differently

• What I needed to do differently

• Clarity about where we’re going

• Creating a shared vision of the business

• Mapping how we intend to get there

• Our roles in achieving that vision.

The outputs from that day were insightful, including:

• A higher appreciation of what each of us brings to the table.

• Organisational structure change through a full senior leadership restructure.

Who would you recommend the Leadership Check-in for?

Every leader should do one! I’ll repeat it again in a year or two. 

I’d recommend the Leadership check-in to every leader with a team of people or stakeholders who wants to grow. Anyone who wants to get better at being a leader, develop their key relationships, and address any challenges within teams. 

It’s particularly useful for leaders whose businesses are going through phenomenal change, like mine.

I started my business as a one-woman band, and I now lead a team of 5 and an associate coach pool of 25+. We’ve experienced massive growth over the last two years. I’ve had to grow as a leader ahead of the business’s growth curve to ensure I remain the best person to be the head of the organisation.

It’s a fundamental step in making sure you’re the best you can be at leading your company through growth.