Leadership Lessons from Basecamp…

Cathy Presland
6 min readMay 13, 2021

…which are actually general (life and work) lessons (of course)

(Long post alert. TL;DR, life happens, it’s not a bad thing, it’s a life thing.)

Leadership Case Study…

Basecamp announced a suite of changes recently, self-described as ‘a full version change’, that caused quite some chatter on the social channels.

It got me curious… what goes on behind the scenes (of the human mind) that causes these kinds of situations? And what options are available to us?

So, curiosity in hand, I thought it would be fun and potentially useful to run a case study. Less for the gossipy chatter and outrage I was seeing on LinkedIn, and not for a critique of what they did, but to see what, as a group, we general lessons we might draw, and what we might see about about leadership and humans at work.

So Far, So Smart…

Great idea.


…part of being human is that not everything plays out in life as it does in our imagination.

The materials didn’t arrive with the participants two days before, as I’d planned, and the first activity… well, let’s say politely that it was completely incomprehensible.

Life Happens…

That’s life, right?


And, no doubt also a microcosm of what happened at Basecamp, and what happens in our lives every day.

Most of the time I don’t think we even notice this disconnect between imagined life and real life; we’re in and out before we’re aware of it.

Problems averted, opportunities taken, our powerful sub-conscious awareness looking out for us and acting on our behalf all of the time.

And then, other times, we notice the disconnect as a niggle of discomfort. Or maybe we don’t always notice it, but we find ourselves digging deeper into a hole in an effort to mute the feeling. I’m pretty sure at least some of that was happening at Basecamp, and me too, briefly, on our case study call.

What’s happening here? Why am I not explaining myself so people can hear it? let me say it again.

Or maybe,

Why aren’t they listening?!!

A sure sign that the very best next step is to stop digging, take a breath, and tune in to what’s actually happening, not what is happening in your expectations.

Human Dynamics…

One thing we agreed on yesterday is that in this world we call ‘leadership’ we are wrangling with humans, in a live system, in perpetual motion, and with a large degree of unpredictability.

When challenges arise, as seemed evident from (our interpretation of) the Basecamp case study, we can forget that’s how things work, and leap to ‘control’. Or we speed up, perhaps at the cost of accessing our all-powerful awareness and the opportunity to respond in the moment to the reality of life.

The fact that we are interacting with humans can be great news or terrible news depending on your perspective-on the one hand it can look like barely contained chaos, on the other it can look like the beauty of the northern lights, or the murmuration of starlings.

What we always have going for us, however, is the feeling of being ‘in tune’ or not. And I was definitely not for a moment there in the session!

Thankfully we are never in it alone-of course we have awareness, but I also had a buddy I’d asked to help demo the first activity repeatedly saying,

Cathy, I don’t understand what we’re meant to be doing.

And what’s cool, and true for all of us, is that we know we’re out of connection, we can feel it in ourselves in the moment, and we can pull back, take a breath and fall back into trust.

Taking ‘Charge’…

The great news, it seems to me, is that humans anywhere, even a small group, together for 90 minutes, let alone those in a larger organisation who can get to know each other and have an ‘endless’ time together, can figure out a way of being in connection that is, hopefully, interesting, purposeful, and enjoyable, at least for most of us, most of the time.

What’s interesting, layering this on top of the case study is to ask,

At one level it looks obvious, it’s my case study, it’s the founders company, there’s a hierarchy, ‘someone’ who can, ultimately, make a decision.

Or is there?

Maybe we just think this is the case and it’s really more like that flock of birds.

Maybe it’s a system which will re-orient and and reshape as it evolves, which will eventually become something other than what you or I or anyone ‘in charge’ requires of it.

And maybe, no matter how much we analyse, there is always something driving these changes that is beyond the human mind to understand, and that we can only experience with a sense of awe and wonder.

I say this because I don’t want you to leap to ‘systems theory’ or some other mechanical understanding that loses the beauty of the whole. and that can put us back into that place where we answer the questions we know the answers to, rather than those we don’t.

Don’t Rush to Answers…

Sometimes we do need to make fast decisions, but I wonder if that’s really as often as we think?

What was very cool (for me anyway) about the case study session is that we were able to draw the general conclusions, that:

1. Every single person comes to the table (or to work) inside their own virtual reality machine, which creates their own, also perpetually changing, perspective, including what’s there right now, how the past looks from today’s perspective, and what’s possible in the future (again, from today’s perspective).

The more we see that’s true for all of us, the more likely we are to be patient and understanding with our colleagues, rather than challenging and disagreeable (back to how much we are in reality, versus our own expectations…)

2. Innovation and creativity live in this space of the ever-moving constellation of human ideas. It might be unpredictable, but it’s predictably unpredictable.

This is great news unless you think you can and should be predicting what everyone thinks, maybe even containing, in reference to (our interpretation of) what happened, at least in part, at Basecamp.

Live Into the Questions…

The point of emphasising these two points of understanding, rather than leaping to prescriptions, is that the more we understand humans and human interactions in the workplace (or anywhere), the better we can find relevant, contextual, thoughtful answers to questions like:

  • what are we here for?
  • what containers do we put around our work and what processes can we design to communicate and collaborate?
  • how do we resolve conflict? how can we allow people to be heard and still, as an organisation, move forward with pace?
  • are we listening? to ourselves and others? are we allowing the space to go deeper than the surface noise?
  • do we accept that growth and change can be uncomfortable and are we articulating that’s where we are? do we say out loud, and with humility, ‘this is a phase that might feel a bit rocky for you. it does for me too.’
  • can we allow ourselves to fall into a space of trust even in the rocky times; how do we keep best interests at heart no matter if the way they show up doesn’t always suit everyone’s preferences.

It was a great place to leave the group, because the more we can tune in to our own radar of what’s happening, and the more genuinely exploratory we’re prepared to be with our questions, then the better foundation we have for creating outcomes that work for the purpose we have in mind.

It reminded me of the Rilke extract from Letters to a Young Poet,

I want to beg you, as much as I can, dear sir, to be patient toward all that is unsolved in your heart and to try to love the questions themselves like locked rooms and like books that are written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.

I know this is a long post, and maybe I didn’t quite explain things the way they sounded in my head so please, if there are parts you’d like to ask about, or challenge me on, I’d love you to reach out and let me know.

With love,


Cathy Presland

Leadership — aka understanding what it is to be human — for people who are making a dent into poverty, redistribution, dignity, and other things that aim to bring us closer rather than drive us apart. I have additional writing here, including regular leadership seminars. If you’d like to explore more deeply or join a conversation check those out or contact me directly if there’s something I can support you with.

Originally published at https://cathypresland.com on May 13, 2021.



Cathy Presland

What if making an impact was part of your everyday? Stories to light up your soul. Read more and free courses: https://cathypresland.com/