Choose your own one on one meeting

This is a "choose your own adventure" game in which you run a one on one meeting with your team member.

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You are Don Quixote of La Mancha, whose calling it is to give aid to the needy of all sorts.
Both you and Sancho Panza are comfortable on your chairs, ready to start your biweekly one on one meeting.
What do you say?

You just put Sancho in defensive mode.
One-on-ones are not bi-weekly performance reviews, not even checkpoint meetings. If you need those, you schedule another dedicated moment to them.
One-on-ones should provide an opportunity to listen to your team members, and this requires trust. Leave competence judgment for another time.

Try to recover from this misstep.
"Actually, forget about it..."

Not a big deal, but you should probably leave the things that you want to say more toward the end of the meeting.
Reserve at least the first half to exclusively listen to your team member.

Move on.
"But it can wait, let me know about you first..."

Even if he doesn't seem to have much to share, Sancho seems glad that you asked it.

"Nah, work is fine."

That's it. Silence.
You need an icebreaker. How do you make him more comfortable?

Now he is clearly uncomfortable. He seems puzzled and stressed.
He is wondering if there is a right way to answer this. Is this a test? He is trying to come up with a witty answer, but that's hard.

"Hmmm... Ah... err..."

Don't try to force "coolness"; this is a conversation, not a talk show.
You better fix it fast.

Ok, no icebreaker, straight to the point.
And it seems to be a good question because he clearly has a top-of-mind answer.

"I would love to travel less. Actually, I would love no travel at all. I miss my wife and daughter when we are traveling and we are traveling all the time these days."

You already suspected this, but you're glad he stated it so explicitly.
Still a hard topic though, how do you reply?

He frequently talks about his family, so it's just nice to ask about them.

"They are great. I am always sending letters. Even though they miss me, they understand the importance of what we are doing. I miss home though. When will all this travel stop?"

Great, good to have him sharing his concerns.
Still a hard question though, how do you answer it?

Not a good answer. He knows the travels will continue to be necessary and he knows you know it too.
In the best case, you created false expectations; in the worst case, you were straight up dishonest.

He remains in silence wondering what's the point of sharing his concerns if the boss is just going to hand-wave them.

Better move on to the next topic and try to improve the meeting from now on at least...

You pulled a "stop whining"? Really? Oh dear, are you even trying?
If you want to be "the boss", giving orders as input and expecting results as output, why even border doing one-on-ones?

Sancho looks like someone who is ready to give up at this point.

There might still be hope. Try to be helpful at least.

Why are you making this about you?
And why do you think he is comfortable to give an honest answer?
You are new to this "one-on-one thing", I assume.

"You are, of course. You are good at... seeing things, you know. You have visions, I mean, vision! You have vision, that's it. That's good... right?"

Yep, that was awkward. What did you expect?
Ask about his job, easy mode for you.

That was awesome.
A straight, honest answer, no BS and still making it on a positive tone. Now you better indeed keep your promise, of course.

"Oh, I look forward to! Let's do this, let's bring justice to the world!"

That was a boost only honesty can deliver!
Now let's find out about how can you help him.

That's always a good question to ask.

"Hmmm... I am basically your squire, right? My role is very clear to me, don't worry."

Ok, all good on this front. Not every question has to surface new concerns.
Move on to broader questions.

It's good to get feedback on your actions while still making the conversation about him.

"Like master like man. He who leans against a good tree finds good shelter."

All good and Sancho is speaking in proverbs now; it seems he is getting more comfortable in this meeting.
Good time to know about his thoughts on the endeavor you brought him to.

It's great to check what he is thinking long term.

"I want to be the governor of my own island. Diligence is the mother of good fortune, so I believe I will get to it in time."

Good, you are both on the same page here.
Now seems a good time to know about his thoughts on the endeavor you brought him to.

Terrible question. It is obviously charged and leave him no room to disagree.
It seems you do not want team members as equals, just submissive direct reports that (pretend to) agree with all your decisions.

"Of course, señor!"

Laconic and formal, sure signs of lack of trust.
Try to revert it by nudging him to suggest something new.

A promising question. One-on-ones are great to find blind spots.


Sancho is making a rather long pause. You are not sure if he is hesitant to say what he is thinking or just can't think of anything to say.
What do you do?

Bad choice. Do not steer the conversation or try to validate your own ideas of what should be different.
You won't find a blind spot if you keep nudging your team members to say things that you already thought about. By definition.

"Yes, that is a possibility."

Fix this, make him go back to what he was thinking.

Silence doesn't need to be awkward.
Respect pauses, allow hesitations, let random thoughts surface during the conversation.

"Well... I think we could choose our battles better."

Sancho is still testing the waters; it is your job to make him comfortable and fully express his thoughts.

Don't conclude a topic that your team member is just beginning to deepen.
Also, do not make promises that things will get better when you are not even sure what is wrong, to begin with.

"Ok, ok, all good then."

And just like that, you killed the conversation.
Surely you missed something he was willing to share. Try to surface it in the next meeting, because this one just went off the rails.

    You lost all his trust. Nothing left to say.
    Schedule the next meeting and hope he doesn't quit in the meantime.

That was rather aggressive.
Don't demand clarity, especially if your team member is touching sensitive subjects.
Ask clarification questions in a non-violent manner if needed or just give them more time to articulate their thoughts.

"Ok, ok, sorry. Do you remember the... giants?"

At least he didn't back off from saying what he wanted.
He is onto something, let him continue.

Perfect, that needed clarification, and you asked for it in a short enough way to not interrupt his train of thoughts.

"Do you remember the... giants?"

He is onto something, let him continue.

You just let some irritation show from this topic that is obviously sensitive for you.
That doesn't help if your goal is to develop trust and surface hidden, but important topics.

"Oh, nothing. It was just an example that maybe we should have skipped that one. No big deal."

And just like that, you killed the conversation.
Surely you missed something he was willing to share. Try to surface it in the next meeting, because this one just went off the rails.

    You lost all his trust. Nothing left to say.
    Schedule the next meeting and hope he doesn't quit in the meantime.

Good. This is a key moment in the meeting.
Control yourself and allow him to say everything that is on his mind.

"I mean, they were really windmills, you know it, right?"

Wow, you were not expecting this discussion to resurface.

You could not help it, uh?
You developed the trust for him to bring back this issue, which is a good thing at least.
You should have listened what he had to say though, not be so defensive and show all that anger.

"Ok, then."

He did not buy it was Friston. Why not?
You will probably never know because you are not willing to give him the chance to talk, to really talk to you.

    You lost all his trust. Nothing left to say.
    Schedule the next meeting and hope he doesn't quit in the meantime.

Ok, you are clearly not comfortable at all discussing this.
Which make it all the better that you are controlling yourself and allowing Sancho to share his thoughts openly.

"No, it wasn't Friston. You know it wasn't.
Your reason is now free and clear, rid of the dark shadows of ignorance that your unhappy constant study of those detestable books of chivalry cast over it.
You can see through their absurdities and deceptions, and I hope that this destruction of your illusions do not come so late that it leaves you no time to make some amends by reading other books that might be a light to your soul."

That was powerful.
You never heard Sancho speak like this. You never knew Sancho could speak like this.
It seems that you just have never provided him with the trusty environment he needed to express himself freely.
After such an honest and powerful statement, there is only one thing left to say:

Ok, maybe loathing books is not the most self-aware conclusion that you could come up with. But you are glad this conversation went well enough so you could hear his truth and make it your own.

This is the importance of well-run one on one meetings that are grounded in trust and honesty.
You get to uncover blind spots and genuinely help your team members.
Imagine if you had waited until your deathbed to come to your senses?

    The End

Trust Level

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This is a marketing effort to attract attention to my product One on One Meeting, a note-taking web app for leaders running one on one meetings.

Don't take it too seriously. I just wanted to experiment with something more fun than writing search engine optimized content targeting well-researched keywords. I wouldn't call it an art project, as I hope this can generate some attention and signups. But it was a fun use of my time working on it, regardless.