The simplest way to establish connection

We fumble through so many workplace conversations, especially the meaty ones that make our blood pressure rise.

The easiest way to stay grounded and strengthen your connection with a colleague? Actively describe what is going on for you emotionally. This means getting above the feelings with enough perspective so you can describe them to another person.

“I’m happy you said that…”

“Thank you. I find what you’re saying really helpful.”

“Hearing this helps me see the situation in a new light…”

“It’s scary to be confronted with this, so I’m feeling that right now…”

“What you’re saying is really causing me to reflect, and I’d like some more time to do that.”

The volume of our own thoughts and feelings is often so high, we can easily assume that what we are thinking and feeling is obvious to everyone around us.

It isn’t until you describe it to them.

Charles Darwin on Why We Write

I came across this via Austin Kleon, quoting Charles Darwin (emphasis added):

“Let the collector’s motto be, ‘Trust nothing to the memory;’ for the memory becomes a fickle guardian when one interesting object is succeeded by another still more interesting.”


[A naturalist] ought to acquire the habit of writing very copious notes, not all for publication, but as a guide for himself. He ought to remember Bacon’s aphorism, that reading maketh a full man, conference a ready man, and writing an exact man; and no follower of science has greater need of taking precautions to attain accuracy; for the imagination is apt to run riot when dealing with masses of vast dimensions and with time during almost infinity.

We write for many reasons, but the most important is to capture and crystalize our half-formed thoughts while they happened, because those seeds of insights are fleeting; and because the act of writing, over time, sharpens both our writing and thinking.

I’m constantly amazed to find that a few jotted notes can transform into some of my most impactful business ideas or blog posts.

And, despite this, I can easily trick myself into thinking that all the important stuff is “in my head” at the times that I don’t bother to write things down.

I know not everyone is going to write a blog.

I’d still encourage you to find a way to regularly capture your half-formed ideas, and to take the extra step of developing them into something—you decide what.

Inevitably, you’ll become a better observer.

And there’s nothing better than stumbling across an old thought you had and turning into something crisp, clear, and helpful.

1:1 with Me

There are countless tools and guides out there for having great 1-on-1 meetings. This First Round Review Article is a great place to start (it even has a Notion template with a Question Bank for Better 1:1s).

But I think the tools only work if we show up with the right mindset to these meetings.

This mindset isn’t: it’s my job to update my boss on what I’m up to.

This mindset is: it’s helpful to have a counterpart who helps me stay on track; helps me ensure that I’m prioritizing the right things; and who can help me troubleshoot when I’m stuck.

This framing strips away the trappings of authority that come with the manager:manage-ee relationship.

One way we can do this is by asking: what conversation would I have if I were having a 1:1 with me?

What questions would I ask myself?

What preparation would I do?

What thinking would happen before the meeting?

What sort of feedback would I give me?

Hopefully, your boss has some perspective and experience that you don’t have, and she brings that to the table.

But 70% of the value of the one-on-one is a structured space to have the conversation that you need to have to help you do your best work.

The meeting is for you, not for your boss.

“Para Espanol, Oprima el Dos”

We’ve all heard this message, when we’ve called our healthcare provider, or our bank, or what used to be the cable company.

“Push 2 if you’d like to continue in Spanish,” is what it says.

In the last two weeks, struggling with the byzantine American healthcare system, I’ve had recorded voices at the start of the customer care maze say this sentence….with the most outrageously, embarrassingly American accent you could possibly imagine. It’s a caricature of bad Spanish.

Only two things could be happening here, one worse than the other:

  1. The company doesn’t know that the Spanish being spoken is abysmal
  2. The company knows that it is abysmal, but doesn’t care enough to fix it

Think about this: if you press the number ‘2’, presumably the company will have native Spanish speakers for you to speak to. Which means they don’t have an access-to-native-Spanish-speakers problem, they have a caring about the customer problem, or a bureaucracy problem, or a “I just do what the boss tells me” problem.

Both ignorance and not caring are a terrible place to end up, but we don’t get there all at once.

We get there because those in charge enable a culture tolerates disengagement, and because those not in charge decide it’s easier to follow the rules or to hide than it is to take things personally and to take pride in all of our work.

Teaching caring at scale is a hard thing to do.

It’s also the only thing that separates us from the gravitational pull of mediocrity.

Do or Do Not, There is No Try

The Princess Bride contains, for me, nearly all of life’s great lessons: about friendship, about love, about never starting a land war in Asia.

But Star Wars, at times, goes even deeper. Who can forget the words of Jedi Master Yoda when Luke is attempting to lift his X-Wing fighter out of the swamp using the Force?

YODA: Always with you what cannot be done. Hear you nothing that I say? You must unlearn what you have learned.

LUKE: OK, I’ll give it a try.

YODA: No! Try not! Do, or do not, there is no try.

So often, our language betrays us, illustrating a lack of commitment, a lack of belief in ourselves, a lack of willingness to own our part in creating a problem. As in:

I’ll try to get that you by this Friday. 

I’ll do my best.

I have to _______.

I can’t do that…

I’m sorry that you feel that way. 

Think about the difference in what we communicate when we, instead, say:

I will get it you by this Friday.

I will solve this problem and get back to you with the solution. 

I get to _______.

I can’t do that yet.

I’m sorry that I made you feel that way.

Our language both informs and communicates our thinking. Being more deliberate about the words we choose shifts how people perceive us and shifts our mindset in the face of new challenges.

The Greatest Unmanaged Risk in Fintech

We often think about the ‘upside’ of social impact data—how it can show that an investment is doing more than a typical investment, because it generates both financial and social return.

But what about social impact data as a way to protect financial value?

This is the unique opportunity that presents itself today in fintech, an industry that is growing exponentially and that has huge potential for creating social value, but also potential to make things worse for vulnerable populations.

I wrote a piece for the Fintech Times on just this topic. Here’s the opening, click here to see the whole thing.

The global fintech market was described in a recent HBR article as investors’ “Goldilocks dream”. This is thanks to its promise of big investor returns and positive social impact. In 2021 a total of 113 new fintech “unicorns” were created. They had the potential of bringing the world’s 1.4 billion unbanked customers into the financial mainstream.

However, while financial access is increasing at a blistering pace worldwide – in Kenya 82.9 per cent of the population had access to high-quality financial services in 2019, up from 26.7 per cent in 2006 – access to digital financial products is neutral from a social impact perspective. Some products have a significant positive impact on customers’ lives. Others though, simply meet an immediate need (to make a purchase or pay off a debt). This results in people being left worse off.

(Keep reading)


Learning from Imperfect People

We do it all the time. Ariana HuffingtonClayton Christensen, Nandan Nilekani, Ngozi Okonjo-Iweala…we have something important to learn from each of them.

And yet, each of them may be flawed in some (or many) ways. This doesn’t mean they have nothing to teach.

And yet, when we encounter non-famous, also flawed people, we are often quick to judge. We instinctively treat them as people we have little to learn from.

They also have a lot to teach us.

There’s something they are great at, something that comes naturally to them, something that makes them special—if we’re open to it.

If nothing else, we can learn from how we find ourselves reacting to them—having a quick mind is one thing, being quick to judgment is something else entirely (and yet they often go together).

Generosity of spirit is a better way to go through the world for so many reasons. One of these reasons is that it helps remove our blinders, allowing us to learn from the person standing right in front of us.

The one who, despite his flaws, we haven’t written off.

Walking Backwards

One of the best ways to protect your knees, to strengthen weak hamstrings and to heal your feet is to walk backwards. By flipping our direction, we enlist our muscles, ligaments, tendons, and nerves in new ways: our hamstrings are suddenly in charge, our anterior tibialis plays the supporting role our calves normally play, our glutes take on more work, and our feet and fronts of our ankles have to find stability with a new set of inputs.

Other than a new form of physical therapy that you can do on the treadmill (our outside—be careful!) we can take some lessons from this flip in orientation.

Some of our most important work is done in teams, and these groupings are like our muscles. Every time a group comes together, we take our familiar roles: a person who speaks up more, and someone who likes to listen; a person who always wants to move things along, another who’s uncomfortable if every angle isn’t explored; an agenda-setter, and a bunch of agenda-takers.

A powerful choice we can make on our own is to switch our roles. If we’re a talker, we choose to listen. If we’re a “yes, but”-er, we become a “yes, and” -er, if just for a few hours. And so on.

Or you can take this a step further by explicitly setting new roles for your team for a meeting (or longer): consciously ask a new person to set the agenda; have the person who always sees the flaw or the risk play the role of pushing things a step further. Ask the big talkers to sit still and be quiet.

The first benefit of this is to identify everyone’s tendencies, as perceived by everyone else. You are then able to ask when playing your expected role helps the group, and when your influence is limited because “that’s what he always says.”

As important, doing this as a group builds new interpersonal muscles. A person who’s never set the agenda out loud says “this is what I think we need to talk about.” A talker has to stop thinking about the next thing he’s going to say and, instead, just listens. A person who always pushes the group forward has to verbalize the risks. And on and on.

All of this will serve as a valuable exercise in both empathy and group dynamics. It’s also a reminder that being a one-note team member minimizes your effectiveness, and it hamstrings (ha!) the groups that you’re part of.

Can Can’t Will Won’t and 3-D Management

In Danny Meyer’s interview on the Tim Ferris podcast, Danny shares the world’s simplest 2×2 for how to think about who on your team to invest in, and how much of your time and energy to give them.

The CAN / CAN’T describes the person’s skill. The WILL / WON’T describes their will.

This gives us a shortcut to understand the people on our teams, those who:

  • CAN and WILL: highly skilled and highly motivated. Your top performers today.
  • CAN’T and WILL: people who don’t have the skills but are highly motivated to learn them.
  • CAN and WON’T: people who have the skills but are unmotivated / have a bad attitude.
  • CAN’T and WON’T: people who have neither the skills nor the will.

How to Spend Your Time?

The first question Danny poses is: how should you spend your time as a supervisor? His answer (which I agree with) is that he has the most time for the people on the top half of the chart, those who:

  • CAN’T but WILL: people who are super-motivated to learn, but just don’t have the specific skills today. It’s hard to teach motivation, dedication, professionalism and pride; it’s much easier to teach skills.
  • CAN and WILL. In some ways it’s easy to just “leave these people alone” because they’re crushing their jobs, but this is exactly the wrong thing to do. Give them attention, praise them, nurture them, both for the impact this has on them directly and because of the positive multiplier effects this will have on your culture.

Then we get to the bottom part of the chart. This is where moving decisively is important, around those who:

  • CAN and WON’T: folks who have the skills but are unwilling or unmotivated. These individuals are likely a drain on your culture, though it’s easy to get tricked into thinking you need to keep them, because they are so skilled. This is a trap.
  • CAN’T and WON’T: a simple category, and where you need to move fastest. These people drag down any organization.

From 2-D to 3-D

Now, there’s the 3-D chess version of this, which is where things get really interesting.

This is another way to illustrate the concept of situational leadership, which is one of the most useful approaches to managing others with the world’s worst diagram.

Here’s my take on how to illustrate this:

The idea is that each person cannot accurately be plotted on a 2D graph of skill and will.

Instead, each job requires a collection of attributes, and each person will plot to a different point for each attribute. For example, a member of your team might show:

  • High will and skill doing analytical tasks
  • High will but low skill in drawing cross-cutting insights from those analytical tasks
  • High skill but low will in checking others’ work for errors
  • Low skill and low will in client relations

How to Manage in Each of the Four Quadrants

In my version of the chart, above, you would mentally plot each of these four skills—analytical tasks, insight generation, checking others’ work, and client relations—on one of the graphs, and, as a supervisor, you’d work with your team member differently on each of the tasks. The supervisor’s job is to be:

  • DIRECTIVE for low skill, low will tasks
  • COACHING for low skill, high will tasks
  • SUPPORTING for high skill, low will tasks
  • DELEGATING for high skill, high will tasks

This is what’s explained in the terrible (but useful) standard illustration of situational leadership. Each quadrant describes three things: the employees’ skill, her will, and her bosses’ desired behavior when working with her on a task in each of the four quadrants.

Pulling it All Together

Our job, then, is to have a mental model of how we think about the skill and will of our employees and use that to determine, in the broadest sense, who to invest in and how much time to give them. This is what Danny Meyer is talking about, starting in minute 50 of the podcast.

And, at a more granular level, both employees and their supervisors have a nuanced job to do as they show up to work each day:  diagnosing different requirements of the job across skill and will; communicating this diagnosis to one another; and then using that mapping to partner differently in support of the execution of tasks and the development of these various skills.

It becomes clear pretty quickly—especially as we think about this over time—what a gross simplification it is to talk about “good” and “bad” employees; or to talk about whether it’s better to be a “hands on” supervisor or one who “gives lots of freedom.”

The reality is that people are a collection of attitudes and abilities for different things: we might love sitting in front of a spreadsheet and hate managing teams; love building relationships and hate writing a budget. Our skills, our willingness to deploy these skills, and the collection of skills that make up our jobs is constantly evolving.

The one constant that bridges people through all of this evolution—from one role to the next and to the next; from one set of skills to the next and to the next—is the willingness to keep on doing one’s best and to continually learn.

And the best bosses are the ones who realize that there’s no one-size-fits-all approach to management, just as there’s no team member who has mastered all the skills she could possibly learn.

The Oldest You’ve Ever Been

Is how old you are right at this moment, of course.

It’s likely you are also the wisest you’ve ever been, and the most experienced.

But what about the strongest, the most durable, the most resilient, the most courageous?

So much of how we experience today comes from the stories we tell ourselves.

Be careful not to talk yourself out of your potential