Your leadership weakness is being “too controlling.” What to do?

17 phrases and suggestions to avoid the common leadership weakness of coming across as too controlling as a manager.

Recently, a manager told me how he’d received feedback from his team about his greatest leadership weakness. “I come across as too intense or controlling,” he admitted.

Genuinely concerned, he then asked me, “What can I do to not be that way?”

Among all the feedback we receive as managers about our leadership weaknesses, coming across as “too controlling” might be one of the most difficult to swallow.

You get that stuck feeling in your throat because, well, frankly, you feel like you need to be controlling, at times. You feel justified. After all, you just want the thing to get done! And record goes to show, sometimes it doesn’t get done. So how else are you supposed to communicate the urgency and significance of a deliverable, without coming across as “intense” and “controlling”? And who said “intense” and “controlling” should be perceived as a negative thing, in the first place?

Keep reading “Your leadership weakness is being “too controlling.” What to do?”

Taking risk without risking everything

Sometimes it’s really fucking hard to trust yourself. Especially when you’re likely to be wrong about some part of the decision. Question becomes which part, and to what degree. I’m in the middle of a number of these types of decisions right now. It can be quite disorienting. While it’s not life and death, I imagine it’s a lot like a non-instrument rated pilot who finds themselves in the fog, unsure where the horizon is, when up feels like down and everything’s a guess. When faced with these situations in the business world, I try to take the most risk without putting everything at risk.

Don’t buy the hiring lottery

It’s never easy looking for a job. Trotting through shitty, vague, unrealistic openings that are frequently been written by people thrice removed from those you’ll eventually be working with. Then hoping to hear back from the black hole that is the application process at many companies. Ugh. No wonder many applicants end up jaded, if stuck in that process for too long.

But sitting on the other side of the process can certainly also make you jaded. Reading through hundreds of applications from people who aren’t even trying. Trying to understand the role or trying to express why they’d be a good hire.

I think part of the problem is the idea that “if you don’t apply, you can’t get it!”, which sorta sounds like a “if you don’t play, you can’t win” slogan for a lottery. That’s a perfectly reasonable conclusion from someone who has gone through one too many black-hole application processes, but it’s also wrong.

Sure, you can’t hit if you don’t swing, but it doesn’t matter how many times I swing, I’m not going to hit a homerun against a Yankees pitcher. Not one in a hundred, not one in a thousand. Yes, step one of being in the game is showing up. But unless step two is being somewhat qualified for that game, you’re still going to lose.

This doesn’t invalidate the idea that there are perfectly qualified candidates who hold themselves back from applying due to imposter syndrome or anxiety or other reasons stemming from a lack of confidence. Boosting that confidence amongst the qualified with encouragement is ace. Let’s keep doing that.

But let’s stop pretending that the hiring process is a lottery. That sending out the most resumes is how you win it. That you should apply to positions no matter how remote of a stretch it is, because, hey, they gotta hire someone, and that might as well be you!

Applying for a job is hard. Every time you don’t hear back, you can lose a tiny little something of yourself. You thus might try just that little bit less next time. So if you keep applying for unlikely-to-get jobs, you might eventually water yourself down, and dilute your application, until it’s a very thin cup of tea indeed.

Don’t do that. Apply when you have a real shot. Stretch a little, but not too much. Save yourself and your ego from the lottery trap.

The 4 essential questions to ask yourself as a leader

Instead of seeking answers, becoming a better leader starts with asking ourselves the right questions.

You want the answer. The silver bullet, the trick, the hack, the leadership best practice, the new manager checklist. There’s got to be some secret point of leverage that you don’t yet know about to becoming a better leader… It has to be out there, right?

We’re obsessed with wanting to know the answer. The 1–2–3 steps to follow so we can right our wrongs and make progress faster.

Yet when it comes to becoming a better leader, I’m not convinced there’s is one. Scholars can hardly agree on the definition of leadership, alone. As Ralph Stogdill famously wrote in 1974, “there are almost as many different definitions of leadership as there are persons who have attempted to define the concept.”

Keep reading “The 4 essential questions to ask yourself as a leader”

We Love the Subs

THEY GOT A PEPPER BAR

In 2004, fast food company Quiznos launched a national advertising campaign featuring animated rodent-like creatures screech-singing an ode to the chain’s toasted sub sandwiches. The TV commercials were instantly polarizing and lodged themselves in many viewers’ brains like a recurring fever dream. In the latest episode of the Rework podcast, the people behind the campaign share the story of how an early Internet meme got turned into an unforgettable ad campaign.. Take a trip down memory lane and relive the moment when a weird, experimental corner of the Internet briefly crossed into mainstream culture. The real treasure is the spongmonkey friends you made along the way!

Basecamp is hiring Customer Support Representatives

Basecamp is looking for two Support Representatives to join our team in providing the best customer support around. 

About the Job
You’ll be responsible for providing tremendous customer service and support via email for all versions of Basecamp and our other apps. You’ll help us answer questions via Twitter, make some customer calls, create and edit help documentation, run personalized demos, and teach some online classes. You’ll also have ample opportunities to carve out your own passion projects related to supporting our customers.

Deep technical knowledge of computer programming is not a prerequisite, however you should be well-versed in basic troubleshooting techniques to solve issues caused by most Internet Gremlins. The ability to think beyond clearing cache and cookies in order to troubleshoot the specific issue that’s reported is essential.

During training, you’ll be expected to be proactive in your process and learn quickly. Once fully up-to-speed (2-3 months), you’ll write about 100 emails per day. This is a significant volume, so be sure that you’re ready and able to deal with that kind of daily load — you’ll get all the support and guidance you need along the way!

About You
We’re looking for some great writers who love helping people, so you should enjoy making complicated situations simple and painless. This means being a great problem-solver with the ability to process and resolve issues quickly. You should be a stellar communicator, even when you have to communicate less-than-stellar news. You should have highly tuned senses of compassion and empathy and a drive to constantly help others.

We have a rhythm to our work and a low turnover rate — more than half of the team has been at Basecamp for over five years. But, your voice matters to us. We make change from fresh perspectives and appreciate new viewpoints, so you should feel comfortable speaking up about your values.

You love supporting people. This isn’t a springboard into another area at Basecamp. You want to be part of our support team for a while, and you’re excited to contribute to making Basecamp the best product for our customers.

A big part of the role itself is supporting each other, so you should understand the value in prioritizing relationships with your colleagues.

We strongly encourage candidates of all different backgrounds and identities to apply. Each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. Basecamp is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career.


About Our Pay and Benefits
Our pay is within the top 10% of the industry, for the matched role and experience, based on San Francisco rates. We also believe in fair, living wages at Basecamp no matter where you live. For a Junior Customer Support Representative, this starts at $70,000.

Our benefits are all aimed at supporting a life well lived away from work. None are about trapping people at the office or cajoling them into endless overtime. Just the opposite. We’re all about reasonable working hours, ample vacation time, summer hours, fitness, wellness, food, education, and charity. See the full list.

If you want to join Ashley, Chase, Chris, Elizabeth, Jabari, James, Jayne, Jim, Joan, Kristin, Lexi, Merissa, Shanae, Sylvia, and Tony in making our customers happy, please apply!

How to Apply
Introduce yourself to us as a colleague. Show us your future here! We value great writers, so be yourself, be creative, and take your time with the application. There’s no prize for being the first to submit! Stock cover letters won’t do. Tell us why you want this job. Tell us about:

  • why you want to work in customer support.
  • why you want to work at Basecamp and not somewhere else.
  • a description of a great customer service/support experience you had recently, and what made it great.
  • a time you taught yourself a new skill to complete a job or project.
  • a guide to making your favorite meal.

Then, pick three of the customer questions below and answer them like you would if you worked here (hint: at this point, we value tone and style over correctness):

  • Does Basecamp 3 offer time tracking?
  • Can I create recurring events in the Basecamp calendar? What about recurring todo items?
  • Do you offer 2fa for signing in?
  • How do I work with clients in Basecamp 3?

Click here to apply. We’re accepting applications for this position until July 5. We’ll let you know that we’ve received your application. After that, you probably shouldn’t expect to hear back from us until after the application deadline has passed. We want to give everyone a fair chance to apply and be evaluated.

We’re seeking fluent English speakers/writers to work with us to answer customer inquiries via email and phone during these hours:

  1. Monday through Friday 9am-6pm CST
  2. Tuesday-Saturday 10am-7pm CST


We’re a remote company, so your location isn’t as important as your fit to the role. That said, we do prefer that your daytime hours coincide with your working hours so as to avoid night shift burnout. Don’t forget to tell us where you’re located!

We look forward to hearing from you!

Basecamp is hiring a Head of Marketing

For the past 20 years, we’ve been passive marketers with a little m.

We speak at conferences and on podcasts, we write books (REWORK, REMOTE, It Doesn’t Have to be Crazy at Work), we share our point of view on thousands of blog posts, we invented a framework (Ruby on Rails) that changed an industry, and we make products that redefine their categories (Basecamp, Highrise, etc.). And right now we’re working on something new that’s going to surprise people.

We’ve gotten by on strength of product, cult of personality, a unique point of view, running against the wind, and incredibly generous word-of-mouth promotion from our customers. We’re fortunate it’s been working. 20 profitable years in business is the proof. We’re naturally proud of that.

But we feel like we’ve begun to saturate our natural sphere of influence, our current reach. Passive marketing can only get us so far, and we have a desire to go further. Today, if we’re in the mix, it’s by chance, not choice. And because of that, we feel a bit invisible outside of those who know us already.

And it’s no surprise: We haven’t really advertised. Or made it easy for new people to find us online. Lately we haven’t explained our brand particularly well. Or thought much about how we’re perceived in the modern market. We don’t show up in places where potential customers hang out, and we haven’t gone far enough supporting and sponsoring events and like-minded organizations. Basically, we’ve never deliberately focused on actively getting the word out, making sure our brand is positioned properly in the market, or meeting customers where they are.

We lack a Marketing strategy with a capital M. It’s time to change that.

Moving forward, we want to be intentional about creating awareness (how do we introduce Basecamp to people who don’t know us?), prompting consideration (how do we get people who need a product like ours to consider us for purchase?), and driving conversion (how do we get people who are considering Basecamp to sign up, pay us, and start using our products?).

So, for the first time, we’re ready to hire someone to lead that charge and own that responsibility. We’re looking for our first Head of Marketing.

How’s that challenge sound to you?

ABOUT THE JOB AND THE WORK
Fundamentally, this job is about developing and executing a broad strategy to bring more people to the front of the funnel by increasing awareness and interest outside of what we’ve already built. We’re not looking for somebody to spend time on email drip campaigns or improving onboarding. While important, this role is much broader than that. This also isn’t a job for self-described growth hackers.

This is a role for someone who knows how to mix a wild idea with a practical pitch. Someone who’s eager (but not annoyingly so) to pick up the phone and negotiate a major partnership deal. Someone who has an eye for talent, a nose for bullshit, ears close to the ground, and the creative mind of a conductor. Someone who’s previously managed large spends and helped a brand transition through a similar process. Someone who recognizes an opportunity when they see one, but knows how to steer clear of high effort low reward mirages. You see things other people miss, and you know how to put leverage to good use.

And while we’ll support your strategy with a multimillion dollar budget and creative support from the CEO, you’ll start this process without a dedicated internal team. While we have designers, writers, and a data analyst occasionally available to assist, we don’t have a marketing department or spare staff focused on everything you’ll need to get done. This means you’ll initially be expected to identify, vet, choose, and manage external vendors or agencies to help pull off your plan. Building an in-house team is something we’ll discuss down the road.

While some may see this as a disadvantage, we think it’s a big opportunity. You’ll be able to pull in the best agencies, freelancers, shops, and creative specialists to help pull off the plan. You’ll bring us creative ideas we’ve never considered in the past. You’ll challenge our thinking and help us see ourselves in a new light.

In addition to big picture strategy, you’ll focus on practical day-to-day work like fielding sponsorship opportunities that come our way. Keeping an eye on analytics. Reaching out to groups, organizations, movements, events, and other brands we should be partnering with. You’ll also be expected to regularly detail progress, setbacks, and marketing insights for the whole company.

We’re aware that at many companies, this is a multi-person position. Someone focused on the marketing strategy. Someone else focused on brand. Someone else focused on partnerships and sponsorships. And so on. We’re not expecting a herculean marketing turnaround with a single person at the start, but we absolutely believe the right person   can point us in the right direction, guide us, come up with campaigns, be resourceful enough to get them produced, manage the process, study the results, course correct, revamp, and try more things. We know someone has to own this, or we’ll end up where we are today.

Bottom-line, this is an impact position. In time, the business should look better with you on board.  A clear case of before and after. You’ll help us be noticed, be seen, and be found. We should also feel better about ourselves with you around. This is a big responsibility and we are here to support you, cheer you on, and make it happen. We’ve talked about having someone like you on board for years, and now we’re finally ready.

ABOUT YOU
You’re creative. You’re organized. You’re experienced. You’ve done this before. You want to do it again. You absolutely want to do it for us.

We value people who can take a stand yet commit even when they disagree. We’ll often subject ideas to rigorous debate, so you’ll need to stand up for what you believe, but we remember that we’re here for the same purpose: to do good work together. Charging the trust battery is part of the work.

Yes, you’ll need to learn how we work at Basecamp, but we’re also looking for someone to teach us how to work. And once we’ve figured that out, be able to share that story with the world. We should tell the story of how we changed our approach to marketing.

We’re not looking for a superhero who thinks sheer hours = good work. Excess doesn’t impress us – creativity and efficiency does. You’ll have 8 hours a day to work, and, we hope, at least 8 hours a night to sleep. What you do with the other 8 is up to you, never to us. You’ll report directly to the CEO.

ABOUT OUR PAY AND BENEFITS
The starting salary for this position is $181,000. You can read about how we set salaries here.

Our benefits are all aimed at supporting a life well lived away from work. None are about trapping people at the office or cajoling them into endless overtime. Just the opposite. We’re all about reasonable working hours, ample vacation time, summer hours, fitness, wellness, food, education, and charity. See our full list of benefits here. In fact, if you’d like you can browse the entire employee handbook as well.

Basecamp is a remote-work company so you can be anywhere, but you’ll need at least 4 hours of overlap with Chicago time in your normal work-day routine.

We strongly encourage candidates of all different backgrounds and identities to apply. Each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. Basecamp is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career.

HOW TO APPLY
We want to get a sense of how you think. To that end, please use your cover letter to share with us your take on the following questions:

  1. Tell us how you’ve taken an existing brand to a new place by revamping their approach to marketing. How would you begin to approach figuring out where we stand and where we should be standing?
  2. Give us an example of a small-to-medium sized business that you think markets themselves particularly well? Who’s doing an outstanding job out there? And why?
  3. Since you’ll need to bring in outside talent to get the job done, which creative agencies or freelancers do you think are doing particularly interesting work? And why?
  4. Share an example of a time great marketing caught your attention and turned you into a customer.
  5. Tell us about something you almost bought recently, but decided not to. What failed to convince you?
  6. What’s inspired you lately? What’s the most creative thing you’ve seen or experienced in the last few years?

We value great writers, so take your time with the application. Keep in mind that we do not equate length with substance, so please keep your cover letter to fewer than 1500 words. Stock cover letters won’t do – tell us why you want this job, not just any job.

Click here to apply. We are accepting applications for this position until June 28th, 2019. We’ll let you know that we’ve received your application. After that, you probably shouldn’t expect to hear back from us until after the application deadline has passed. We want to give everyone a fair chance to apply and be evaluated.

We can’t wait to hear from you!

How Buffer Meets Up

Even remote companies need actual face time every once in a while. That’s why Basecamp holds companywide, weeklong meet-ups in Chicago twice a year. Fellow remote tech company Buffer has 85 employees across the globe that get together once a year for an annual retreat, and they’ve visited countries from South Africa to Iceland. On this episode of the Rework podcast, Carolyn Kopprasch of Buffer talks about the kind of work that gets done during this time, helping introverts manage energy during an intense week, and her favorite parts of Retreat.

Why wear a watch when I have the time on my phone?

As a “technology person” (ugh), people ask my why I wear a mechanical watch when I already have the time on my phone?

I love mechanical watches for a number of reasons – the art, the science, the ingenuity behind the mechanisms, the continuation of a craft dating back centuries, the look, the feel, the freedom from batteries and tethers and cords.

But lately it’s really come down to this: When I look at my watch, it gives me the time. It asks nothing in return. It’s a loyal companion without demands.

In contrast, if I look at my phone for the time, it takes my time. It tempts me. The time is paired with notifications. The time is paired with a big color screen. The time is paired with a temporary cure for boredom. It seduces. It’s a rare moment that you look at your phone and you only see the time. I don’t like that trade.

I use my phone when I need what my phone does. I use my watch when I need the time. I like being on time, I like knowing where I stand in the hour, in the morning, in the afternoon, in the day. I look at my watch a lot, and I just love that it doesn’t look back.


Thanks to Krys for the insight.

Habits always form

After a recent talk I gave, a student came up to me and asked me for one bit of advice for someone’s who’s still in school but about to graduate.

I’ve always found these questions difficult to answer. For one, It’s been 25 years since I’ve been in college. I don’t remember what I wished I knew back then, and today I know even less about what would be useful to know right now.

So I backed off a specific, and shot for a general.

The advice was this: Habits are always forming. No matter what you do, you’re also forming habits too. Keep that in mind with whatever you do.

When we talk about habits, we generally talk about learning good habits. Or forming good habits. Both of these outcomes suggest we can end up with the habits we want. And technically we can! But most of the habits we have are habits we ended up with after years of unconscious behavior. They’re not intentional. They’ve been planting deep roots under the surface, sight unseen. Fertilized, watered, and well-fed by recurring behavior. Trying to pull that habit out of the ground later is going to be incredibly difficult. Your grip has to be better than its grip, and it rarely is.

So be aware of what you do, what you’re doing, and how you’re doing it. Every do digs deeper. Every does grips stronger.