Observations From 20 Mentoring Sessions with Managers Over 30 Days

In February, I launched a free mentoring program for managers. I wanted to give back to the communities that have so greatly impacted me in my career, and I saw a dearth of free options for managers who are looking for guidance but can’t afford a full-time coach.

My program is exceptionally simple:

1. My sessions are like floating office hours. I’ll do one 45 minute session per day, and my calendar is public.
2. Anyone can sign up, and you can do repeat sessions if you’d like (already have done repeats).
3. Any topics are fair game.
4. It’s totally free. This is not a funnel. I’m not selling you anything. I’m not pitching you anything.

My audience has been almost exclusively managers from Hacker News, based on a handful of posts I’ve made in threads referencing my program and offering up guidance. I haven’t known any participants, save for one person, who was once a colleague.

Observations

Below are a handful of observations others might find helpful about the types of topics that are impacting other managers. I’m going to be intentionally vague about specifics to protect the anonymity of those I’ve met with.

One On Ones are the Most Discussed Topic

Almost every session I’ve done has involved discussion about 1:1s. After reviewing my session notes, I recorded in 50% of the situations where 1:1s were brought up, the manager saying something to the effect of:

I don’t feel like my 1:1s are very productive.

Some managers highlight that they don’t feel like they do enough in those conversations to talk about growth and development. Others highlight that they feel like they just devolve down to status updates. In essence, the reasons why they “are not productive” vary, but the feelings seem to be common.

One thing I’ve anecdotally observed is that managers seem to, on average, do weekly one on ones for short periods of time, rather than longer one on ones on a slower cadence (think bi-weekly). My bias/hypothesis is that these frequent 1:1s discourage complex conversations, which typically are at the root of a growth conversation. Instead, they encourage bite-sized topics like status updates, company pass downs, or drive-by feedback.

Before I give any of my suggestions on how to do 1:1s, I try to throw up a disclaimer to ward people off of my advice:

There are dozens of ways to run a one on one. Focus on finding the structure that practically works best for you and your team members, not the one that is the “best practice” for 1:1s.

But, most people want to know what you do/recommend, so my list looks something like this:

1. Run 1:1s bi-weekly for 45 minutes.
2. Sessions should always last for the full 45 minutes. This is particularly important early on to discourage those who are shyer or less prone to talk from being quiet to try to shorten meetings.
3. Avoid using 1:1s for “feedback that stings”. What I mean by “feedback that stings” is the type of feedback that might demoralize, frustrate, aggravate, or trigger defiance in the other person.
   
   Feedback should be specific, actionable, and timely, and waiting until an upcoming one on one is unlikely to be timely. In addition, building up a negative connotation with your 1:1s isn’t going to engender a positive mindset prior to the meetings. You want your people to look forward to 1:1s, not dread them.
   
   I’m pretty sure this opinion is slightly controversial, and other managers can reasonably disagree with this position. If you STOP giving constructive or challenging feedback because you stopped giving it in 1:1s, then that’s almost assuredly worse than reserving that feedback for your 1:1s.
4. Reinforce positive behaviors during 1:1s. If you pointed out something positive in the moment, that’s great! Take the time in your 1:1 to bring it up again: “I know I said this to you earlier in the week, but the attention to detail on your proposal to the executive team was superb. How can we find ways to have our entire team have that level of detail in the work we do together?”
5. Have conversations about growth and development on a periodic basis, and set calendar reminders to help you remember to have the conversations. At this point, I don’t have a recommendation on what the cadence should look like. I’ve seen anywhere from monthly to quarterly be effective.
6. If you don’t feel like you know how to have a growth and development conversation, look to help your company craft a career map / role rubrics. I really love what Circle-CI has done, and I recommend it broadly.
7. It’s fine for both sides to have agenda items for 1:1s. I know some people say that managers are only there for the report’s agenda, but I think the meeting is best when it’s bi-directional.
8. If you can, go for a walk. I’m a huge fan of walking one on ones. Buy your team member a coffee, or a smoothie, or whatever makes them happy. If your company won’t reimburse you, do it anyway.
9. Iterate on your process. It should evolve and adjust for every person you add to your team. Don’t be afraid to add and ditch pieces that aren’t working, or experiment on new things. It’s fine to tell your people, “Hey, I want to try something” and have it not work.

Concerns tend to be people oriented, not conceptual

When I ask upfront in my intake questionnaire what people want to talk about, they tend to list conceptual ideas. These high-level concepts often look something like:

How can I improve the feedback culture on my team?

Interestingly, whenever I start to unpack a question like this during one of my sessions, they tend to devolve down to a specific individual that is the catalyst for the conversation. That isn’t to say that the manager isn’t deeply interested in improving the culture all around, but it’s usually one person that triggers the manager to begin thinking about how to solve this problem.

This seems to be a natural side-effect of team scaling. Participants continuously observe that inflection points during a hiring process preceded issues. This isn’t an unexpected side-effect of that process, but I’ll often hear a follow up that sounds like this:

Is there a way for me to improve my screening process to prevent issues like this?

I tend to push back on this as a screening issue. Homogeneity in the needs of your hires is likely a fool's errand. You may be able to get away with it for one or two hires, but if you scale up to have five or more people, there is going to be diversity in needs no matter how hard you try to filter it away.

At a more basic level, having homogeneity is detrimental for team growth. Team members pushing colleagues to grow and improve is an important part of the development process.

Uniformity will lead to stagnation.

Stagnation will lead to attrition.

Attrition kills morale.

There are lots of happy managers out there

One might think the cohort of people who would hop on a call with a stranger offering to do free mentoring to managers would be people who are thinking/wanting/planning to leave their job.

That is absolutely not the case.

The managers I meet with tend to love their colleagues, enjoy their work, and are seeking to help deliver tangible improvements. I truly did not expect this when I set out to start my program, as I figured the anonymity that meeting with a stranger provides is conducive towards people “looking to bail”. But, this hypothesis seems to have been resoundingly wrong, and I’m really happy about that.

Looking For Someone To Talk To?

Head to my website and grab a slot! I tend to be booked out a week in advance, so it’s always best to grab a slot sooner rather than later. We can always reschedule if need be.