Oh, Those One-On-One Meetings….

Recently, I have been rereading CS Lewis’s autobiography, “Surprised by Joy.” If you have not tackled this one, I highly recommend spending some time with it. Lewis has a unique way of really opening my eyes to some fascinating ideas and contrasts. One that struck me was his approach to European poetry. For a long time, there was an order that the greats were to be read, like the Iliad and Sohrab (in that order). Lewis approached the reading of these classics and made this observation:

“It does not matter at what point you first break into the system of European poetry. Only keep your ears open and your mouth shut and everything will lead you to everything else in the end.”

I thought, what a powerful message for leaders. Keep your ears open, have some empathy, keep your mouth shut, display some impulse control, and everything will work out for you in the end. 

How many times do we not do that? We get mad, spout off, stop listening, have no impulse control, and then make bad decisions and are filled with regret. 

Sometimes leadership is about patience, humility, and relationships. Maybe MOST of the time leadership is about these things. 

Linking Lewis to Leadership

As I was reading the above section in Lewis’s autobiography, I was wondering where leaders could work to apply the lesson of “keeping your ears open and your mouth shut”. I had even done some journaling around this and nothing was coming to me.

Then I had a call with one of my coaching clients, who wanted to discuss his approach to one-on-one meetings with people on his team. 

When I probed him about the genesis of his question, he lamented that he and his direct reports just didn’t have that much to discuss. Especially to warrant an hour every week or two.  He felt up-to-date on their progress by the emails he received. And he felt the meetings were a bit forced and awkward.

As we continued our discussion, it became apparent to me that this leader was focused very much on the tactical outcome of his one-on-ones. This is the “what” conversation is all about. In this part of the conversation, the person on the team focuses specifically on the tasks they are working on, “what” they are doing.

What I noticed might be missing in the conversation were some of the weightier opportunities for “how” his leaders were acting, “how” they were making choices, and “how” they were motivating and inspiring the teams that report to them. Then second after “how” is “why” they were doing what they were doing. “Why” did they make a certain decision, and “why” did they think a particular action was motivational or inspirational?

These more strategic elements of a conversation take some curiosity on the part of the leader. If the leader has a good question around “what” the associate is doing, then they can implement Lewis’s idea of opening your ears and shutting your mouth. 

One on One Philosophies

After we finished this discussion on having productive one-on-one conversations he asked if I had any philosophies on the one-on-one meeting. 

 I do indeed have some philosophies on one-on-ones. Every good philosophy should have a pillar or two on which it is built. So let me offer this as the anchor to my take on the one-on-one meeting.

Philosophical Pillar: People need to feel connected to their supervisors.

The one-on-one meeting is the opportunity for you to connect the associate to yourself and the organization. This is where you build your relational trust. So your focus and undivided attention are necessary for the associate to feel heard and understood. 

Rules of Engagement

I think to build trust, you need to have some rules or boundaries. These need to be communicated to the associate. 

You can set your own rules, just keep in mind the philosophical pillar and ensure the rules you set along with your philosophy.

Here are my 4 rules for engagement in one-on-one meetings:

  • Associate sets the agenda. If the supervisor has a need they should set up a separate meeting.

  • If the subordinate has nothing to update, then they cancel the meeting. The supervisor never cancels the meeting, they can only reschedule and it has to be within 1 working day. Too many canceled meetings mean that I am not building the kind of trust I need to be effective as a leader.

  • For the subordinate, I suggest 4 types of one-on-one meetings. Alternating between these types helps to prevent the meetings from being monotonous. 

  • I like a weekly meeting cadence, alternating between the 4 types. 

4 Types of one-on-one meetings

  1. Project updates- Usually occur biweekly

  2. Professional Development- Occurs monthly or every other month

  3. People update- Occurs monthly or every other month

  4. Strategic Vision-Quarterly

So it might look something like this as it is implemented:

Week 1- Project update

Week 2- People update

Week 3-Professional Development

Week 4- Strategic Vision

Week 5-Project update

Week 6-People update

Week 7-Professional Development

Week 8-Project Update

Week 9-People Update

Week 10-Professional Development

Week 11-Project Update

Week 12-Strategic Vision


The Leader sets the expectation

I think the most important thing to remember is that you as a leader need to set the expectation for what these meetings need to look like. Then turn the implementation of the meeting over to your associate. If you give them the big picture and the framework, you then have the capacity to open your ears and really listen to the associate. Helping them feel valued and heard is a big part of what your leadership is all about.