Jason Fried's Blog, page 11

What great managers do: Prune

Being a great manager and English gardening have more in common than you might imagine.



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If you want to improve your leadership skills, there no shortage of analogies that have been made about great managers.

A great manager is a “coach,” a “captain of a ship,” or even a “human shield.”

However, I heard a more unlikely comparison about leadership made on our podcast, The Heartbeat, when I interviewed David Cancel, CEO of Drift. He told me:

“I kind of think about most of this stuff as English gardening. If you want an English garden most of the work is actually the pruning and the taking care of. It’s not the planting, it’s not the plant selection. It’s this constant pruning. The day that you stop pruning is the day that the garden is full of weeds and overrun.”

I found this to be a brilliant analogy on several levels.

First of all, pruning is a small, seemingly minor activity. You’re not making big, sweeping moves of planting new shrubs or replanting a whole tree. This is also true of good leadership. We often believe great managers must take broad, bold actions. Strong decisions, rousing speeches, uncharted direction. But that’s not really what leadership is. It’s is not lavish, nor massive. It’s small, incremental action that engenders real progress in the long run. True leadership is genuinely saying “thank you” when a team member does a favor for you, or asking “How could’ve our last one-on-one meeting been better?” before you meet with a direct report.

Second, when you prune, you clip away the dead leaves or diseased areas of a garden to encourage healthy growth. A great manager does this, as well. They focus on removing frustrating blockers for their team – be it changing an unrealistic deadline, or deciding to fire a rude customer. They figure out what parts of the team are in decay or lacking in resources. Great managers focus on paring back, and then getting out of their team’s way.

Pruning is also done periodically, only when the season is fitting. If you prune all the time and you can accidentally over prune a plant and deprive it of nutrients. Leadership is similar. Harvard Business Review published research revealed on how managers who are “constantly coaching” overwhelm their team and exhaust them. After studying 7,300 managers, they discovered “employees coached by Always-on Managers performed worse than those coached by the other types.” Constant coaching, like constant pruning, is a bad thing.

However, at the same time, fail to prune consistently over time, and, as David mentioned, your entire garden will be overrun. Weeds sprouting, stems rotting. As a manager, you must be mindful of this. You can’t expect that a single one-on-one meeting with your direct report, once a year, will be sufficient for understanding their thoughts on what could be better about the team. A regular, steady cadence of communication – especially for one-on-one meetings – is critical if you’re to feel connected to your team as a leader. In both leadership and English gardening, “one and done” doesn’t work.

Thank you, David, for making this analogy. Who knew pruning English gardens could be a source of inspiration for us as leaders.

Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

Hire When It Hurts

You may have noticed that Basecamp is in the midst of what qualifies around here as a mini hiring boom: five open positions across customer support, programming, and ops, as well as a newly created marketing role. The company has received more than 4,000 applications and every single one is read by a human being. In the latest episode of the Rework podcast, hear about why Basecamp briefly lifted its hiring freeze, how job ads are written, and what the process is for evaluating candidates.

Am I micromanaging my team?

Here are the 5 most telling signs of micromanagement – and what you can do instead.



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I won’t tell anyone:  You think you might be a micromanager. Argh. If there were scarlet letters for a bad manager to wear, “m-i-c-r-o-m-a-n-a-g-e-r” would be among them.

But, how do you know if you’re a micromanager, for sure? 

Yes, you can directly ask your team members if they think you’re micromanaging them. If you have a direct report who has a penchant for shooting you straight, I highly recommend this. (In fact, when we asked through Know Your Team to 606 employees across 61 companies, “Do you feel micromanaged?” 12% said “Yes.”)

But it’s also probable that your direct report might not concede the truth. You are their boss, after all. And telling a boss they’re a micromanager is the equivalent of, well, slapping them in the face.

Six Hours of Phone Calls

Been asking some close business friends for SEO consultant recommendations. Getting some back. Curious to see if there’s overlap with the broader audience. If you were going to hire an SEO consultant to audit + make recommendations, who’s the obvious go-to?

— Jason Fried (@jasonfried) May 13, 2019

When Jason put out a call on Twitter for SEO consultants, he received dozens of responses. In order to choose someone to work with, Jason and Basecamp designer Adam Stoddard interviewed all of the candidates in one six-hour block of back-to-back phone calls. They sit down with Shaun in the latest episode of the Rework podcast to discuss why they’re looking for SEO expertise, how they conducted the interviews, and what it’s like to shop for something you know nothing about.

Leverage? No thank you.

Since we began including salaries in our job postings, a few people have asked if it affects the leverage we have over candidates.

The suggestion is that if we tell people exactly what we pay for a specific position, and they would have accepted less, but we’re now on the hook to pay them more than we “needed” to, then they have a leg up on us rather than us on them.

I find this line of thinking abhorrent.

I have zero interest in having leverage over anyone in a hiring situation. Of course we get to choose who we hire – so, yes, there’s power inherent in the act of hiring – but other than that necessity, leverage is the last thing I’m looking for.

Remember, I’m looking to to hire someone to work with, not work against. Starting things out with “look what we got away with!” seems like a terrible start to what hopefully develops into a wonderful, long-term working relationship. Leverage need not apply.

Announcing “Shape Up”, a deep dive into how we work

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Back in 2006, we self-published Getting Real: The smarter, faster, easier way to build a successful web app. It was our first foray into broadly sharing how we work at book-scale. It struck a nerve, turned heads, and changed minds. It offered product people, designers, and developers a way out – an escape hatch. They could finally ditch their way of working that wasn’t working for a new way that would.

Since then we’ve released a number of books, all focused on the business end of things. You could learn how to run a company from REWORK, REMOTE, and our latest mass-market release, It Doesn’t Have to Be Crazy at Work.

Today we return to our roots. Nearly 13 years after Getting Real was published, we offer the spiritual follow-up. Today we introduce Shape Up: Stop Running in Circles and Ship Work that Matters. This web-based book explains how we work in replicable detail. It’s comprehensive, yet approachable. A recommended read for anyone involved in software development. And it’s 100% free to read online – we don’t even ask for your email address.

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Why now?

Over the last few years, there’s been a renewed, heightened curiosity about how we work at Basecamp. People often ask us how we get so much done so quickly at such a high level of quality with such a small team. And how we keep our teams together for years and years. We’ve written some blog posts about it, but the topic really demanded a book-length effort.

For one, we’re not into waterfall or agile or scrum. For two, we don’t line walls with Post-it notes. For three, we don’t do daily stand ups, design sprints, development sprints, or anything remotely tied to a metaphor that includes being tired and worn out at the end. No backlogs, no Kanban, no velocity tracking, none of that.

We have an entirely different approach. One developed in isolation over nearly 15 years of constant trial and error, taking note, iterating, honing in, and polishing up. We’ve shaped our own way. This book is for explorers, pioneers, those who don’t care what everyone else is doing. Those who want to work better than the rest.

But ultimately, don’t think of this as a book. Think of it as a flashlight. You and your team have fumbled around in the dark long enough. Now you’ve got something bright and powerful to help you find a new way.

We hope you find it interesting, enlightening, and, most of all, helpful.

Let’s read.

The hardest leadership advice to follow

We all know we’re supposed to “work on the business and not in the business” as a leader… but what holds us back? And, how do you exactly put “stepping away” into practice?



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“Work on the business, not in the business. Pause. Step back. Take stock. Reflect. “

This is some of the most ubiquitous advice I’ve received from leaders on our podcast, The Heartbeat, over the past few years. Yet, as often as it’s repeated, I wonder how often it’s followed.

I’m writing about myself here, namely. Yes, conventional wisdom says to “sleep on it”, to step away from the work to get a fresh perspective on it. And yes, I’ve vigorously nodded my head in agreement whenever someone espouses something along those lines. But, if I’m being honest with myself, how often do I personally act on that recommendation?

For the longest time, my answer has disappointingly been, “Not often”. Prior to last year, I didn’t regularly set aside blocks of meaningful time for myself to reflect on the business. When faced with a critical decision to make or a tough situation to resolve, I plunged myself deeper into the work.

“More, harder, faster” was my default setting. Is it yours, too?

Sinking in

Sometimes, a thing has to smack me aside the head for it to sink in. Case in point: It wasn’t until I’d accumulated the mass repetition of the advice, “Step back, reflect on the business,” over and over again, that I woke up to the obvious wisdom that’d be staring me in the face all these years.

My ears perked up, in particular, this past fall when I interviewed Natalie Nagele, CEO of Wildbit. I asked her about the biggest lesson she’d learned running her multi-million dollar company for the past 17 years, and she said this:

“In order to truly lead, we have to have time to think and to really step back and work, as cliché as it is, on the business and not in the business. You know that it’s important. You read about how important that is. Everybody tells you how important it is. All your mentors do it, but you’re still a small business and you’re stuck in so much of the day to day.”

Natalie’s words resonated with me. She admitted firsthand how it’s a well-known platitude to “work on the business and not in the business.” And yet, she also admitted how hard it is to do in practice. (What a relief, I wasn’t alone!)

But why? What keeps us from doing this thing, that so many of us know is good for us as leaders to do?

The big hairy monster of “now”

The biggest culprit in the room is the urgency of the situation we’re in. Some giant, hairy monster is in front of us now, waving his hands madly, saying, “We can’t afford to slow down, and stop doing something. Someone just put in their two weeks notice. A client is (rightfully) freaking out about a poorly delivered project. Another client is giving you a hard time (unjustifiably) about something you have no interest in doing. Two team members are having a personal dispute and you’re going to need to step in. Oh, and that new potential hire you were so excited about? She just accepted another job so you have to go back to the drawing board for that role…”

For many of us, the hairy monster doesn’t stop yelling, he doesn’t stop waving his hands. Especially, in a small team, it’s all we can keep our eyes on.

How many hairy monsters do you have bopping around?

Making the monster less scary

Natalie had an insightful response to our tendency to be focused on the unexpected problems, the sudden fires, the hairy monsters constantly in our view. She told me that those hairy monsters of big decisions and tough situations are “a lot scarier when you’re in the business than when you take a step out.”

For instance, let’s examine the hairy monster of a key person about to leave. Whether it’s a walk over lunch or a day you take off to mull on the situation – the reflection will likely lead more lucid thinking. You’ll have time to ask yourself questions like: “What’s the worst case scenario? Can we replace this person? Does this person leaving open an opportunity for us to improve our culture in some way?”

Distance and time from a problem often removes the fear, insecurity, or anxiety associated with it. As a result, you can act with clarity and decisiveness. You’re not posturing nor pretending things are great – rather, you’re choosing to see things for what they are. You can respond, instead of react. You can see that the big, hairy monster isn’t so big and hairy as you initially perceived.

Looking back, the best decisions I’ve made have been in this way: With thoughtful deliberation, careful time set aside, and a true stepping away from the business, be it for 10 minutes, 10 hours or 10 days. And the worst decisions I’ve made? They conveniently have all been made when I was rushed, flustered, or fearful.

Similarly, Natalie shares how her worst decisions were made when she didn’t take the time to step away. She leveled with me: “I’ll come back to [a decision I made under stress] three months later but that was a really bad decision, like, ‘We should have not have reacted that way.’”

In my interview with Joel Gasgoigne, CEO of Buffer, he attested to this as well, sharing a metaphor that likens the mind to a glass of water. When he is first faced with a difficult decisions, Joel describes:

“I’ll now just say ‘I’m not in the right state of mind to make this call right now, I’m going to go away and think about it, just overnight.’ It might not take long. It might have taken an hour from being away from that. Then this cloudy glass of water settles, and then I have this clear mind on it. Usually for me, that’s when I have the epiphany of, ‘This is the right thing.’”

So, how do we clear our mind, and make our glass of water less cloudy?

Letting the water settle

Natalie shared how she regularly schedules 3-day retreats with her husband and business partner Chris to go up into the woods, and focus on a particular issue. Nick Francis, CEO of Help Scout, took a month-long sabbatical, coming back truly refreshed and clear-eyed from the vacation (you can read more about his experience here). When Bill Gates was still CEO of Microsoft he would take a week off every year to sit in the woods and think without any distractions. And, John Donahoe, former CEO of eBay, has talked about how he takes a “thinking day” approximately every three months.

For myself this past year, I’ve scheduled one half-day – either on Monday or Friday – every week for long-term thinking about the business. And then, every month, my business partner Daniel and I will take a full day to do a strategy session. It’s our way to clear the muddy water, to chase out the hairy monsters, to work on the business and not in the business.

If you don’t already take time to step back and reflect on the business, perhaps now is the time. Don’t, like me, wait until tens of other successful leaders have told you how helpful it is for them.

This truism is true for a reason.

Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

It’s high time to rewrite the hiring script

The disconnect between how many companies claim that they only hire the best and how they try to actually do that is perverse. A depressing number of job postings are barely more than a list of technology or process requirements paired with an arbitrary desire for years of irrelevance. That’s then fluffed up by a bunch of trite rah-rah bullshit about the supposed glory of hiring company. Ugh.

It really doesn’t have to be like this, but it’ll continue to be like that until companies drastically change their hiring script.

Let’s start with how the process is driven. Far too often, hiring is made someone else’s job. Not the responsibility of the team leader nor subject to input from future coworkers. Instead, the job posting is written by someone in HR or the executive who’s too far removed from the domain or the specifics to do a good job.

Second, the matter is rushed because “we need someone yesterday” and “how hard can it be”. No wonder most job ads look like they’ve been cut from the same template because they probably have! Writing a good job posting is hard because it requires you to actually think about what the position entails and how to realistically portray the organization it’s within. This takes time.

At Basecamp, we have no illusions that we’re going to hire “the best”. In fact, even thinking about candidates in such absolute terms is nonsense. The world is full of people who are stuck doing mediocre work in a shitty environment or blessed to do stellar work by virtue of an elevating one. Most people are well capable of doing both! The only thing that makes sense is to hire the best – defined as most complementary to the organization – person out of the candidates who apply.

Which is why taking the time to describe the role, the work, and the organization with clarity and honesty matters so much. The vast majority of potential candidates in this world are not going to apply to your position in any case. The aim of a great job posting is to expand the pool in awareness of that fact. To entice those complementary candidates to apply who might otherwise wouldn’t have. Dropping this “the best” nonsense is a start.

So that’s what we’ve tried to do with renewed vigor over the past few months here. We’ve been in an uncommon hiring spree with five open positions recently. Every single one of those involved a prolonged, careful process of crafting the best job posting we knew how. Yes, some of the framing is similar between the posts, but each one was written for that particular position. Then subjected to critique, review, and editing by a broad cross-section of future coworkers. I think it shows.

It’s a banal statement that hiring is some of the most important work that an organization does. But that doesn’t make it any less true. Although perhaps the endless repetition of that thought has dulled most people to its wisdom, and they’ve failed to act as though they believe it.

Next time your company is hiring, try to get involved. If you like the way we write job postings at Basecamp, feel free to be inspired, but do the authentic work to make them yours. Your next hire will thank you!

Not too proud to ask

I hear from people all the time who’ve been following this blog, read our books, been loving Rails, become impressed by a job post, or been inspired by a conference talk we’ve given. It’s intensely gratifying to hear how something you put into this world has had a chance to affect someone. Especially when the impact was large enough to open up a novel perspective or prompt real change. It warms.

But it also disappoints when I ask whether the person has tried Basecamp and the answer is “oh, I haven’t, we use [some assortment of big tech / valley combination] – hadn’t even thought about it”. Though the disappointment is not so much in the person as in ourselves. We’ve failed to do the work; failed to draw the connection.

Part of it is the lazy assumption that since you’ve been around for a long time, then of course people who like your philosophy or perspective would know what you make, and would have given it a try. We’ve been making Basecamp for over 15 years, so that erroneous assumption has had a long time to fester.

But that’s not how it works. If you want people to give your product a chance, you gotta ask them. Most companies do this via marketing budgets. They ask a bunch of strangers to try their product that they’ve targeted through the mechanisms of surveillance capitalism. We’ve historically been pretty hands off on ad spend, and remain staunchly opposed to invasive ad targeting.

What we’ve done instead is rely on the goodwill and word of mouth that making, sharing, and teaching affords. And it’s worked well, but it isn’t automatic. You have to activate that goodwill, if you want it to translate into sales that sustain all that making, sharing, and teaching. I don’t think we’ve done a great job at that lately. We’ve taken it for granted.

But how do you ask people who might not be your friends, but don’t feel like strangers either, if they’d try your product? Not just once five years ago, but regularly, without coming off as an annoying, self-promoting shill? I think that’s still largely an open question, but I’m really interested in trying to find the answers.

While we search, though, I thought I’d just remind myself to keep it simple and to keep it direct. So I’m not too proud to ask: Have you given Basecamp a try recently? If you like how we think about work, culture, and people, I think you’re going to like how we make software too. We’ve poured all of us into Basecamp. It would mean a lot if you’d give it a try ❤️

Scrutiny is the prize of success

There’s an unfortunate pattern amongst the Silicon Valley set whenever a startup heralding from their midst is subjected to even mild scrutiny. It’s perhaps best illustrated in its archetype by this tweet from Paul Graham:

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