Secret weapon for manager of managers - Manager Guidance Sessions

Looking back at my journey in building, one major personal development was transitioning myself from a manager of 20+ direct reports to a manager of managers. Though I started to introduce layers in various teams, building out a full executive team soon became a top priority. It was a new challenge for me and I tackled it with a similar approach like many challenges we faced before: put something lightweight in place, learn and iterate. Out of the many trials and errors, one of the techniques that really stood out was something I borrowed from Radical Candor - Manager Guidance Sessions.

Manager Guidance Sessions as described by Radical Candor’s Kim Scott, “commonly called a 'skip-level meeting… The process is straightforward: First, let your managers know that you’ll be scheduling a meeting with their direct reports. Get them comfortable with the idea, and make it clear that this meeting is intended to be helpful to them. Then explain the process to the reports, again making it clear that the goal of the meeting is to help their boss be a better manager — and that the meeting is not for attribution.”

We used Manager Guidance Sessions as a way to provide actionable feedback to managers. We started conducting them quarterly then every 6 months (turned out people didn’t iterate as fast as code.) I conducted all Manager Guidance Sessions for my direct reports. As we established the practice, I coached a few of my managers to conduct the sessions for their reports who were managers. So who conducted Alex’s sessions? ;) Our head of People Operations, Meredith, was gracious enough to do the honor.

In conducting the sessions, we used the simple framework of Start Stop Continue but many retrospective frameworks would do the trick. I started by having everyone in a room and asked everyone to provide at least one item on the Continue list (protip: easier to get people talking about what’s working first.) I never let anyone off the hook with a “no comment”. Everyone must provide one item. The conversations usually would be pretty free flowing and someone’s comment might trigger some agreements and disagreements among the team. We would log the different points of views and specific examples in the notes. Once the session was completed, I would clean up the notes, organize them into themes and share the notes with only the participants to check for accuracy and clarity. After 24 hours, the notes were shared with the manager. Then either in our regular 1:1s or another dedicated time, I would go through the session with the manager and create a plan of attack to address comments from the session. Six months later, the session began with reviewing improvements from the previous session.

To give a sense of how this works in practice, here is an excerpt of the output from my March 2018 session. This was lightly edited for length and to protect the innocents.


Managing Us

What’s Working

- Likes how hands off he is

- There when you need him

- Has a calm demeanor in 1:1s - helps to calm us down

- We don’t have to censor ourselves, can just blurt things out

- Open to disagreement

- Argues in a healthy way

- Lets us make our own mistakes and learn from the fall

What to Improve

- More mentoring

- Would like to receive the same “attention” we give to our teams

- More professional development in topics like:

- Building teams

- Career

- More professional development for people on a “standard” track

- track that’s not going to lead anywhere very differently

- Alex to add items to our 1:1 agendas

- Help us set goals and monitor those goals more regularly AND

- Retros for why goals weren’t met

- dig into those reasons

- more backward-looking

- Customize 15 five for managers

- Can this team create their own questions?

- Feels a bit micro-manage-y (½ of the team wanted this)

- Use the content from the 15 five to inform the 1:1 agenda

- More acknowledgment of what was accomplished

- engage more in the comments/content from 15 five

- Make me feel more valued and appreciated

- More social outings,

- company-wide and leadership team,

- need to “blow off steam”


What’s Working

- Takes process seriously

- Relies on frameworks for decision making

- Follows up, sometimes a bit too much

- could trust a little more on the little things that I will follow-through

- Proactive and action oriented

- Doesn’t let things stale out

What to Improve

- Include direct manager in decisions that are about to be made

- Gray area on workstream lead vs. product manager

- More clarity on company-wide tasks

- More lead time to prepare for offsite and other big tasks


Manager Guidance Sessions are not for every team. At, like many startups, we talked a lot about being a transparent company. Though I’ll venture to say that we are part of the minority that truly took the principle to heart. We stuck with it not only when it was easy but also when it was hard and inconvenient (a topic for a different post.) Manager Guidance Sessions were key tools in delivering on the transparency promise, providing a venue for the reports to voice their perspectives with the support of their peers.


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