I was watching “The half of it” on Netflix over the weekend (a lighthearted comedy-drama written by an ex-Microsoft software engineer-turned-writer, Alice Wu) and a scene in the movie just happened to succinctly summarize a common problem I see almost daily at work. The smart loner Ellie, is trying to coach popular-jock Paul, on the art of conversation so that Paul can charm his high school love interest:


In a subsequent ping-pong scene, Ellie says to Paul “match energy, match strokes, and just say one thing”, which is an apt sporting metaphor for the basic skill of communicating with another.

In this note, I’m going to try and cover interesting things I know about improving communication between people to achieve mutual understanding. I borrow heavily from the techniques of analysis from an unpopular branch of psychology from the 50’s called “Transactional Analysis”. The philosophy of Transactional Analysis isn’t all that relevant (and largely outdated) but its methods of analyzing the back-and-forward between people (called ‘strokes’, just like the ping-pong metaphor) that are highly relevant to achieve mutual understanding.

I will try and cover:

  • Techniques for analyzing and measuring the “strokes” we’re using while communicating with others - the energy, tone, emotion, focus, and agenda.
  • Analyze and measure the strokes of those we’re communicating with (our partners).
  • Understand, predict, react, and respond to the stroke differences between us and our partners to achieve the best communication outcome: mutual understanding.

If you’ve walked out of a 1:1, or a group meeting before with a feeling of “I didn’t feel heard”, or “I have no idea where we landed with X”, or “I don’t know why Joe and Jane didn’t get on the same page”, then this note might help you analyze and answer the question of why.

Let’s start with techniques for measuring and analyzing strokes.

Measuring and Analyzing Strokes

When I’m having an important conversation with anyone, I have a mental ‘background thread’ running in my brain trying to measure and categorize what I say, and what my partner is saying over time. That background thread is either asking questions of myself, or categorizing the strokes we’re playing in real time, like:

  • What is my agenda right now and why do I have that agenda?
  • What is my prediction of my partners agenda or unmet needs?
  • What (if any) emotions am I feeling?
  • What is my prediction of my partners emotions?
  • What is the body language of my partner saying?
  • Is there a power imbalance between us?
  • Is my partner feeling heard and understood?
  • Is there sufficient psychological safety?
  • Am I deceiving, or being deceived?
  • What does the tone, emotion or focus of what I’m saying need to be to satisy my partners unmet needs?

Answering these questions in your head generates the data necessary to pursue the ultimate question:

  • Have we’ve achieved mutual understanding? And if not, why not?

It may seem like an overwhelming list, but after lots of practice (and applying some measurement tricks) it becomes automatic. One example of a excellent measurement to answer the question of “is my partner feeling heard and understood” is to count how many times they say “Yes, but…”. The higher the count, the higher the probability they don’t feel heard. Another simple trick to address my partner feeling heard: try and measure the ratio of time that they’re speaking vs. you – the balance might need to be different depending on the kind of conversation, but a good general rule is to err on the side of listening more than talking.

Answering these questions helps categorize what kind of “strokes” are currently being played, and if they’re the right ones to achieve mutual understanding.

Let’s look at some of these question categories in more detail:

What’s Your Agenda? What’s Mine?

When starting communication for something important, it’s likely you and your partner have a pre-existing agenda, and often, they’re different. It’s important to know what those agenda’s are, and how their existence and their differences might get in the way of mutual understanding. In relationship therapy (the romantic kind), they say “an agenda is like an invisible wall between you and your partner” and it’s the most common category of mis-stroke that gets in the way of mutual understanding.

Agenda mis-strokes might look something like the following, a simple conversation between team mates:

  • Player A: “I don’t feel like my career is progressing as fast as it should.”
  • Player B: “Have you thought about focusing on skills for the next level?”
  • A: “Yes, but I don’t really have enough time”
  • B: “Why don’t you clear some time in your calendar for learning?”
  • A: “Yes, but then it might mean I don’t get enough work delivered.”
  • B: “You should talk with your manager about expectations”
  • A: “Yes, but I’m worried my manager will react poorly.”
  • Awkward silence, frustration.

This is trivialized example but it will get us started on analysis of strokes. What do you predict is the agenda of Player A? What about Player B? Had B accurately predicted A’s agenda, what might have she done differently? Had you been given one line of A’s dialog, I’d first assess the agenda as “A wants some help/coaching for their career issues”. By the second or third A response, I may re-categorize A’s agenda as “blow off some steam and frustration”. B started with “I’m going to help”, and never course corrected. A didn’t get what they really wanted, which was a friendly ear for a bit of venting. “Yes, but” counting would have generated a signal to reassess, and most importantly, change strokes.

The important learning here is how to do the analysis and not the particular example. When you’re starting out analyzing strokes, it’s best to analyze post-hoc conversation: just think back to the back-and-forward, and reflect on the questions above. Upon reflection, was there an opportunity to change your strokes for a better outcome of mutual understanding? Once you’re practiced enough at post-hoc analysis, you’ll be able to move these questions to the background thread of your mind, while you’re in the moment.

Let’s look at some others:

Power Imbalance

It’s rare for two people involved in a conversation to hold equal power, as differences in power are influenced by a large range of things: structural (manager, subordinate), gender, age, experience, knowledge and so on. Unaddressed, this imbalance significantly decreases the probability of mutual understanding, as those with power tend to more easily pursue their own agenda without objection, and those without power tend to become more restrained, silent, perhaps subservient. Analysis of strokes between players tends to reflect that dynamic over time. In the workplace (and particularly within dysfunctional teams), this can look like collective ‘yes-men’, where critics of the work tend to self-silence, and objective data will be looked at through a lens favorable to the agenda of those in power.

For those with more power: ensure that you see active strokes of disagreement and debate, alternative view-points, free expression of thought. Express vulnerability as a tool to ’re-balance power’. For those with less power: catch the emotional reaction of “holding back” during conversation. For both players in group settings: observe the rest of the players, find the silent, and encourage and promote their voices.

Emotional Strokes

This topic deserves its own detailed note as it’s complex, and can have the most negative impact if not handled well. In lieu of that, here are three examples of emotionally driven strokes to think about:

  1. Destructive: stonewalling, contempt, criticism, defensiveness. From any player.
  2. Your own emotional reaction influencing your partners strokes
  3. The emotional reaction that your partner is having, but not visibly sharing.

All three have a high probability of getting in the way of the core goal of mutual understanding, but (1) in particular, has almost zero chance of achieving the goal. Here’s an example set of transactions between a manager (A), and a report (B) who manages a several teams, but one in question we’ll call ‘Team X’:

  • A: “I have been observing one of your teams ‘Team X’, and I’ve formed a weak view that they’re not really delivering what they said they would. What’s going on here?
  • B: Exasperated “Oh what? Team ‘X’ is amazing, they’ve been working hard on delivering FizBuzz widget, Acme product and all sorts of other things. I will set up a review with them and you immediately. The picture you have is completely inaccurate.”
  • A: “Oh, sorry-sorry – I’m sure they’re amazing, but I want us to talk through their results to get a better read of the situation.”
  • B: Still exasperated “I’m sure it’s that they’re just not communicating their achievements well enough. You meeting with them will solve that problem”.
  • A: Annoyed “Yes, but …”

Both players in this set of interactions play flawed strokes: ‘B’ reacts emotionally, playing defensive and slightly contemptuous strokes. ‘A’ plays two flawed strokes, (1) the opening, being a closed form question which may be interpreted as criticism of the manager or their team, and (2) reacting with annoyance that the intent of the original stroke was misunderstood.

Both players could have pivoted early to increase the odds of mutual understanding. ‘B’, instead of defensively countering, could have asked an open-formed, curiosity seeking question like: “Oh interesting. I’d like to learn more about the signals you’re seeing, and your general impressions of the team”. ‘A’, when seeing ‘B’s strong defensive reaction, could have gone two ways: (a) change focus to the ‘meta’ of the defensiveness, trying to understand why they got exasperated/defensive, or (b) addressed the misplayed opening stroke which caused the defensiveness in the first place.

Emotional reactions tend to be re-occurring patterns for individuals. It helped me to sit down and think about my own patterns of emotional reaction: I don’t respond well to individual criticism; get extremely upset at perceived violations of trust; get overly-righteous at situations of injustice, etc. And often, my reactions in these situations can look like TM ‘B’ above: aggressive, defensive, contemptuous. I’ve learnt techniques to capture these emotional reactions before they escape my mouth, improving the odds of playing better strokes for more productive outcomes.


I always say “trust is safety” or “replace the word trust with safety”, as I think that safety among peers and partners more clearly represents what is required to have an effective partnership and to increase odds of mutual understanding. It’s also a useful word to generate requirements for effective transactions between people:

Not safe:

  • Treading cautiously, focused on ‘saying the right thing’.
  • Worried about reaction
  • Closed off, hiding
  • Fearful
  • Unable to predict reaction
  • Unable to predict flow of interactions

Safe: essentially being the opposite of the above. And I’d put special emphasis on ‘prediction’. The better someone is able to predict you, the more likely they’re going to feel safe with you. Without safety, anything of significant meaning or anything “high stakes”, has minimal chance of achieving mutual understanding.

It therefore follows: improving safety is about increasing predictability between players, increasing neutral and positive interactions, increasing shared realities/mutual understanding.

Accurate Prediction is Everything

Remember the desired goal here: to understand, predict, react and respond appropriately to strokes between you and your partner in a way that improves the odds of mutual understanding. To sort of ‘get in a flow state’ between players, where both players feel safe enough to play their full, unabridged, most impactful strokes.

What is required for this:

  • accurate assessment of your own reactionary strokes (emotional in particular), and pivoting where necessary
  • accurate prediction of reactions to, and interpretations of, strokes (for both you and your partner)
  • understanding of how the environment influences strokes (power imbalances, agendas, politics), and adjusting your strokes as necessary

A perfect interaction would be playing “perfect strokes to your partner, and them back to you”. But as mentioned, strokes are predictive and based on models that you and your partner build of each other over time - models are probabilistic, which is why we talk about ‘improving odds’, not ‘achieving perfection’. This also implies that we need to help our partners build a better model of us, so as mentioned in ‘safety’, we should add:

  • enable our partners to improve their predictive models of our strokes, by being consistent, predictable.
  • enable our partners to feel that we’re open, transparent, safe, and adaptable when stroke differences occur.

The more transparent and predictable you are, the safer people feel. This improves odds of people you work with raising hard issues, pushing for more diversity of thought, and giving you feedback early.

Getting Started

It’s a long note, so I’ll summarize the recipe:

  • Measure your own strokes
  • Measure your partners strokes
  • Analyze (either in the moment, or post hoc) those measurements
  • Adjust strokes to improve odds of mutual understanding

It’s difficult to do this in real-time to begin with, so I’ll offer a simple way to get started: recruit an observer. In this period of VC only, it offers opportunities for others to watch strokes in real-time for you, and give you feedback on your interactions with others. Think about how you think the conversation went, then ask your observer for their observations, see how well they match.

In 1:1 settings, try keeping a pen and paper handy so you can jot down quick notes on the flow of conversation for post-hoc meeting analysis.

Doing this repeatedly will force your brain to upload the measurement and analysis into your ‘muscle memory’, for real-time use.


  • Mutual Understanding is hard, but better communication techniques can improve the odds of achieving it.
  • Measure and analyze your conversations
  • Understand common ‘conversational blockers’ like safety, agenda, power imbalance