These past months

I have been writing about leading with more honesty. Self-awareness, seeing yourself clearly. The No Ego it takes to keep growing when you would rather feel certain. Courageous authenticity, saying the hard thing, and building a team where others can too.

Each step has moved outward, from you toward the people you lead. This one goes all the way there. It is about relating, real connection.

And here is the uncomfortable part. The relationship you are surest about may be the one you understand least.

The truth you do not get

We worry about the relationships with obvious friction. The tense one, the difficult colleague. At least those are honest. You know where you stand.

The real risk is the relationship that looks fine. Pleasant. Easy. The person who always agrees, always delivers, never pushes back. You file them under no problem here and look away.

But people only tell you the truth once it feels safe to. So a smooth surface is not proof the relationship works. Sometimes it is proof the truth has stopped reaching you.

The easy relationships are the ones where you are least likely to find out you are wrong.

I have been on both sides of this.

I will go first.

I am a late night worker. It is how I catch up. So for years I sent messages at night, on weekends, on people's holidays, whenever I was working. In my head it was nothing, just me clearing my list. I never expected anyone to reply. (My email signature even said as such).

One person told me, long after we stopped working together, that she had been frustrated - for years - about working all hours for me, and upset she had never said so. She always replied, and I took it as her being on top of things. It never once crossed my mind what a message from the boss at 11pm feels like to get.

And it was not just her. I did this with everyone, for years. So now I have questions I will never get to answer.

How many others felt the same way? How many minded and never said? How many, because they liked me, stayed silent? I will never know.

I have also been on the other side. People who know me will tell you I am the last person to hold back the truth. Which is why this might surprise them. I once spent two years quietly unhappy with a leader, and he had no idea. Every time he gave me feedback or asked me to do something, I nodded. I agreed. I kept it smooth.

From where he sat, all was well. The nod told him so.

Both times, someone was sure a relationship was working. Both times, it was not.

But shouldn't they just speak up?

Here is the objection I can feel you having. If they were unhappy, that is on them. They should have said something.

But look at my two years of nodding. I am, by reputation, the last person to hold back. And I still held back. Part of that was my own weakness. I avoided it. I told myself it was not the right moment. And part of it was that I never felt he really wanted to know.

That is the point. People will be avoidant. If the truth depends on them being brave enough to push past that, it will rarely reach you. The person with more power owns more of whether it travels at all.

Their silence is not their failing. It is your information.

But what does it cost me?

Maybe nothing. Maybe a lot. You cannot know, because this is the part you cannot see.

Which is the wrong thing to get stuck on. The better question is simpler. If this relationship matters to you, isn't not knowing worth a look?

You do not need a proven cost to want to understand someone you work with closely. And let us not wait to be ghosted, or handed a resignation letter, to get curious about how someone was feeling all along.

Your choice to make

None of this sits only with the leader. I could have spoken sooner, and I should have. The other person has their own choice to make.

But you cannot make their choices for them. You can only make yours. And yours is to stop assuming you understand, and find out.

The question worth sitting with

A while back I wrote about your cup, everything poured into you before you had the wisdom to choose it. Relating asks for something harder than looking at your own cup. It asks you to step into someone else's, and from in there, look back at yourself.

That is hard to do alone. We are so sure of our own good intentions that we rarely feel how they land.

But you can start with one honest question. Pick a relationship you are sure is fine. Not a hard one. An easy one. And ask

Do I actually know how this person experiences me, or have I just been assuming?

Sit with it. You may find the relationship you were surest about is the one hiding the most.

This week, sit with the question. On Thursday, I will go further into what real connection takes.

If this has sparked some curiosity, I would love to continue the conversation at diane@ptminsights.com.