The one weird trick to great 1-1s

If you’re an engineering manager, you’ve probably read plenty of blog posts, articles, tweets, and books that talk about how to hold successful 1-1s with your team. Your company may even use tools such as 15Five to manage 1-1s with your direct reports. These platforms offer handy tips and tricks to running your 1-1s, from recommended formats to suggested activities.

I have a ‘first one-on-one’ template that I use regularly and share with others, so I am certainly not discrediting any of this.

All of this advice can feel overwhelming. How do you know when to try one tool over another, what questions to ask and which coaching techniques to use?

It’s not easy, but there is a simple trick to great 1-1s.

What is a 1-1?

A 1-1 is any conversation you have with someone who reports to you. Ideally, you’re holding these on a regular basis with each of these people.

Many different things go on in 1-1s. Status updates, career development discussions, coaching, collaborative problem-solving, conversations about business strategy, team dynamics, goals, concerns, confusions, disappointments, opportunities… the list can go on.

Everybody’s 1-1 is different. Each person you manage is an individual, as are you, and you are both continuously developing. Your relationship, team dynamics, and business operations are always changing too.

Therefore, there can be no set formula for a successful 1-1 because no two conversations are the same.

Okay, if there’s no formula, what is the one weird trick?

How can you learn to be successful at something that varies  every time you do it? Sure, as you hold more 1-1s in your career and different situations arise, you’ll become more confident at handling these kinds of conversations.

For example, you can pretty much guarantee that you will experience at least one difficult conversation about salary during a review. You can usually predict who you are likely to have a difficult conversation with and prepare for it. There will also almost always be a surprise though, and someone you didn’t expect will hit you with a hard question or push back on you.

Similarly, you may have prepared feedback in advance but you’re not delivering a speech, you’re starting a conversation, and you can’t predict where it will go.

Even in a 1-1 that you expect to be routine, there may be an unexpected look on somebody’s face and suddenly and it turns in a different direction.

But one thing about 1-1s never changes: a 1-1 is fundamentally a conversation between two people in a relationship. Whatever your purpose for a particular 1-1 may be, the conversation must contribute to building and maintaining that relationship. You simply cannot coach, help, offer guidance or maintain mutual trust and authenticity with your employees if you do not put effort into the relationship.

How do you do this? By showing up and being present for the conversation that actually happens instead of being preoccupied by the one you were expecting.

I don’t mean don’t bother preparing. There’s a whole other article I could write about how to prepare for what you believe will be a tough conversation. But it is not a presentation that you can control, it’s an improvisation that you try your best to guide.

In Free Play: Improvisation in Life and Art, the author, Stephen Nachmanovitch, describes a conversation with a doctor friend of his in which they talk about what  improvisation has to do with the practice of medicine:

“In real medicine you view the person as unique – in a sense, you drop your training. You are immersed in the case itself, letting your view of it develop in context. You certainly use your training; you refer to it, understand it, ground yourself in it, but you don’t allow your training to blind you to the actual person who is sitting in front of you. In this way you pass beyond competence to presence.”

The one weird trick to great 1-1s is presence.

Okay, so how do you cultivate presence?

Oh c’mon, you know how. Or rather, the seven different meditation and/or sleep apps you have on your phone, or your yoga teacher, or that article you read in a business journal about cultivating mindfulness in the service of productivity (sigh) – they know how. You cultivate presence through practicing mindfulness, both by yourself, so that you have awareness of how your own mind works and how your own body feels, and when you are with others.

I can’t tell you which ways of practicing mindfulness as an individual will be the most fruitful for you. But here are some things to keep in mind as you show up with presence to your 1-1s.

Pay attention

What is the other person saying? What are they not saying? What is their body language?

What’s their energy like? Calm, frustrated, tired, scared, excited?

Pay attention to what’s happening now, in the moment. Respond to what is actually happening in the moment, not what you planned for or expected.

Watch the other person and listen when they speak; notice when they’re pausing, rather than  concentrating on what you’ll say next. If you’re focused on what to do next, you’re not paying attention to what’s happening now.

“But when do I figure out what I’ll say next, then?”

Get comfortable with silence

One of the most moving thank yous I’ve ever received was after a really tough conversation with an engineer who had said some regrettable things in an email to someone else at the company. They thanked me for making room for silence in the conversation.

No one had thanked me for silence before. So I started thinking about silence, and its place in conversations, especially difficult ones.

Sitting in silence during a difficult moment can feel really uncomfortable. If you’re the person who is ‘supposed’ to know what to say next, taking time for silence to formulate a response can feel terrifying. How long before the other person gets tired of waiting and demands some kind of answer, whether or not you’re prepared to give it?

If you’re the one ‘waiting’ for an answer, leaving room for silence demands that you also remain silent, not pressuring, and don’t let impatience overtake you. Show compassionate awareness while the other person either eventually comes up with an answer, or, perhaps, you can ask, “would it be helpful to take some more time to reflect and return to this conversation later?”

Allowing silence is a real gift to anyone who you are in conversation with, and it’s a real gift to yourself too. Take the time to be silent when it’s you who needs it.

Get comfortable with silence while you reflect.

Okay, but what if I reflect in silence for a while and I still don’t know what to say? Then what? What good is presence now?

Get comfortable with not knowing what to say

When you’re not spending all of your time in a conversation planning your next move, you’ll need to get comfortable admitting that you don’t know what to say. If you’ve taken some time and you are still not sure what the best response is, say so.

First, thank the person for having shared something or asked a question to which you have no good response:

“Thank you for sharing that.”

“I can see this is an important question that deserves a thoughtful answer.”

Then admit you don’t know what to say yet:

“I’m not sure how to respond.”

“I don’t have a good answer for that yet.”

“That’s a perspective I haven’t thought about.”

“I’m not sure yet how to advise you about this.”

Then you say, “let me take some time to reflect and get back to you on that.”

If you’re anything like me, sometimes you’ll try to respond before realizing that you don’t have the answer. I do that all the time. No big deal. Just back it up and start over:

“Wow, I realized I’m just saying things so I can have an answer, but this is something I actually really need to think about. I’m going to stop myself now and take some time to reflect so I can give you the thoughtful answer this deserves.”

Sure, sometimes you’re in joint problem solving mode with someone and it’s fine to just spitball with them. If that’s the case, make sure you clearly identify that you’re only brainstorming or spitballing. This is really important because if you’re talking to someone who reports to you, then every word you say carries extra weight – make sure that you have established the relationship and are clear on how much weight you’re putting on your words so that the other person doesn’t think you’re mapping out a plan when you’re just talking things through.

I do not recommend trying to ad lib your way through really difficult issues without any preparation. Part of responding in the moment is recognizing when you shouldn’t respond in the moment.

Finally, be aware of your own feelings

While you need to pay attention to the other person, you also need to be aware of  your own feelings. If you’re talking to someone who reports to you, you can’t dump your feelings on that person.

If you’re anxious, disappointed, angry or confused, you need to manage these emotions. If you become overwhelmed, you need to recognize that it’s time to break from the conversation and come back to it. If you end up, say, unintentionally losing your temper or shouting at an employee, it will be unbelievably damaging to your relationship, your company culture and, most importantly, the employee themselves.

There are lots of ways to tell someone that you need something more or different from them; they all work better than yelling.

If you’re in a 1-1 and you notice your own feelings getting out of control, get out. When this happens to me I just say: “I’m having a lot of feelings right now that I need to go away and deal with. I’m going to take a break from this conversation and get back to you when I’ve processed them more.”

In conclusion

“Other people, for all the heartache they cause us, still represent the best opportunity we have to make sense of our lives.” – Twyla Tharp, The Collaborative Habit.

Like all weird tricks, presence is simple but it’s not easy. If you commit to practicing it, though, you will get better at it, and when you show up fully to your 1-1s, you’ll get better at those too.

You’ll navigate difficult conversations with more confidence, knowing when you need to simply hold space, ask a question, take a moment to form an answer or reflect. You will recognise when you need to break and pick up the conversation later, and when you need to bail immediately so that you don’t react impulsively.

All of this will help you build strong, trusting relationships with your employees. The more you model this and build trust, the more they too will be increasingly able to fully show up, not just to conversations with you, their manager, but to all of the conversations that they’re having with their colleagues.

This practice goes beyond individual 1-1s to influence how the whole team can work together, improving everyone’s capacity to collaborate gracefully with their coworkers. Nobody is perfect and we are all capable of causing frustration, annoyance, and even heartbreak for one another  – but the more we are able to show up for one another in difficult conversations, the better we get at working together.