A Step-by-Step Outline for Starting a Tough Conversation

Let’s say you need to deliver some critical feedback. How do you kick off the conversation?

Maybe you get straight to the point and rip off the band-aid. Just go straight for the jugular.

Alternatively, maybe you start with a simple question, “How are things going?” Your hope is that they bring up the issue and save you a mountain of worry. Obviously they know something is wrong, right?

Critical conversations can be awkward. There’s this giant elephant in the room, and it’s tough to find the right approach to talk about said elephant.

I’m just finishing up Fierce Conversations by Susan Scott. The book provides a structure for having “fierce” conversations, which Scott describes as:

[A conversation] in which we come out from behind ourselves into the conversation and make it real.

In a more practical sense, fierce conversations are those in which we can truthfully attack an issue that’s probably difficult to acknowledge, have an honest conversation, come to a shared understanding, and set some kind of action plan to address the root issue moving forward.

Scott describes the perfect 60-second intro to a fierce conversation. Having flubbed my fair share, I found it to be a helpful template to avoid some of the awkwardness and get into the meat of the conversation.

Continue reading “A Step-by-Step Outline for Starting a Tough Conversation”

What Does “Buy In” Really Mean?

My colleague over at Automattic, Simon, recently kicked off a discussion inspired by this talk by Janice Fraser at Mind the Product.

The talk expands on three key points related to work and life, but it was her final point that stuck out – “You Don’t Get Buy-in in a Single Meeting”.

Fraser mentions that she isn’t a fan of the phrase buy-in for several reasons.

  • Nobody knows what it is.
  • Everyone thinks they have it.
  • Once we get it, we forget about keeping it.

She then introduces an acronym “UBAD,” which stands for understanding, belief, advocacy, and decision-making – the core components of getting everyone onboard with a direction/vision.

I’d encourage you to watch the entire video, but today, I wanted to share some thoughts around generating buy-in and overcoming the hurdles Fraser identified.

Continue reading “What Does “Buy In” Really Mean?”

2018 Retrospective

Each year, I set aside an hour or two to reflect back on the previous year and look forward to everything I want to accomplish over the upcoming year. I’ve been doing this since 2015, and it’s been a helpful exercise to focus my energy heading into the new year.

This year has been pretty crazy. We had our first son; we spent several months off as a family on paternity/maternity leave; and I changed roles at Automattic. It was a fun ride!

A few Saturdays ago, over tacos and a delicious IPA, I took some time to reflect back over 2018 and set up an action plan for 2019.

(Previously: 2015, 2016, and 2017)

Continue reading “2018 Retrospective”

Designing for the Extremes

Having worked in Customer Support for some time now, I’ve become quite obsessed with customer experience.

I’m the nerd that notices bugs in software I use on a daily basis. I also make a mental note of both confusing and delightful user interfaces. I get frustrated when buttons I expect to do one thing do something different entirely.

I pay attention to these things because they matter…a lot. As we’ve talked about before, there are far too many options available for customers to choose from. If your product experience sucks, it’s really easy to find a replacement. Boom – you’ve lost a user forever.

On the flip side, I also think there are a ton of quick wins that instantly upgrade the experience and win over customers with little time investment. The language you use in copy, the way in which you highlight key actions within your product, the accessibility of your contact options – they all play a huge role in delighting the people that pay your bills.

On a recent episode of the Tim Ferriss podcast, I was re-introduced to a thought exercise from Brian Chesky of Airbnb – designing for the extremes.

Continue reading “Designing for the Extremes”

How to Effectively Delegate and Avoid Stealing Success From Your Teammates

Time for a scary admission: I can be a bit of a control freak.

For the longest time, if I was asked about my biggest weakness, I would say just that – I have a hard time letting go of control especially if we’re talking about managing a project or a complicated task. I was the kid in school that preferred to work by himself rather than in a group (yeah…that kid). I knew I would do the project correctly. Someone else? They might screw it up.

As a result, I’d pile on tasks even if I was overwhelmed. If I took it on, I knew it would get done. That was all that mattered! If I did hand something off, I’d be sure to provide step-by-step instructions on how to get it to the finish line.

This might be a bit of an exaggeration. I’ve been steadily trying to get over this fear of letting go especially after I read Marshall Goldsmith’s What Got You Here Won’t Get You There. I’ve gotten better at handing over tasks and allowing others to run with ideas. Still, it’s an area that I’m constantly trying to work on – how to delegate effectively and allow others to crush projects on their own, without my needless meddling.

This concept of effective delegation popped up again recently as I read The 7 Habits of Highly Effective People. One of the habits (Put First Things First) spoke to this idea of delegating ideas. It broke down two types of delegation – Gofer and Stewardship – and described how the former steals success from teammates while the latter empowers them.

Let’s dive in.

Continue reading “How to Effectively Delegate and Avoid Stealing Success From Your Teammates”

Juggling Roles

Over the past few weeks, one idea has surfaced again and again through podcasts, books, and articles I’ve read:

Multi-tasking (or having multiple priorities) is the key to failure. To succeed, you must identify one thing that takes precedence and accept mediocrity at everything else, so the prevailing wisdom goes.

This message has come up several times over the past few weeks from reading The ONE Thing by Gary Keller to a discussion with Angel List founder Naval Ravikant on the Spartan Up! podcast to an interview I listened to with Greg McKeown, author of Essentialism. I think it’s worth separating out what I see as two different types of multi-tasking:
  1. Trying to do two different tasks at the same moment in time (like trying to watch TV and also listen to your friend tell a story).
  2. The multi-tasking we all do on a daily basis as we juggle the various roles we all play (team member, writer, husband, mother, father, etc).
It’s well documented that the former variation doesn’t work. You’ll get a much better return on investment by single-tasking – devoting all of your energy to one task at a time. Read Deep Work if you’re not convinced. The second variation – juggling the many roles we all play on a daily basis – is where I tend to disagree with the prevailing wisdom. Continue reading “Juggling Roles”

Humility and Curiosity

Over the past five months, my wife and I have been adjusting to our roles as new parents. It’s a stressful gig! There are endless amounts of diapers, sleepless nights, and fits of crying for no apparent reason. Of course, there are also moments that make it all worthwhile – the smiles and giggles that now fill my phone.

Parenting comes with an immense amount of responsibility. Not only are you charged with providing for this little human, you’re supposed to raise him into a respectable adult. The pressure!

There are countless online articles listing out values we should instill on the younger generation for a better tomorrow. I know because I’ve spent quite a lot of time reading about them. Even before he was born, my wife and I were pouring over a list of 30 rules we wanted our son to adopt; maxims like: “In a game of HORSE, sometimes a simple free throw will get ’em.” and  “If you need music on the beach, you’re missing the point.”

I recently finished reading Factfulness, an insightful book about why the world is in a better place than it might appear. I have a lot of highlights from the book, but one in particular stood out as I had this idea of raising a respectable little human running through my head.

Most important of all, we should be teaching our children humility and curiosity.

Continue reading “Humility and Curiosity”

How (and Why) Do You Protect an Idea?

In the 19th century, Francis Cabot Lowell stole an idea. More importantly, he stole an idea from Britain and brought it back to the United States, largely transforming the American economy.

The target of Lowell’s espionage wasn’t exactly sexy, but it was effective nonetheless.

In 1784, Edmund Cartwright, an English inventor, pioneered the mechanical loom. For many years prior to his invention, looms (a tool for weaving fabric) were powered manually. The invention led to a drastic increase in output and productivity.

As a result, Britain’s textile industry boomed, and they fought hard to protect the source of their dominance. It was illegal to sell power looms to manufacturers outside of Britain and textile workers weren’t allowed to emigrate to other countries for fear that they would spill design secrets. British customs officers even searched visitors as they left the country.

Enter Francis Cabot Lowell.

As author Matt Ridley describes in The Rational Optimist, Lowell made a trip to Britain and visited a number of mills around the country. During his stay, he memorized the details of the power loom and brought them back to the United States. When he returned, he had a mechanic and inventor turn his memories into a close replica.

Idea stolen.

Continue reading “How (and Why) Do You Protect an Idea?”

Do Hard Things With Good People (and Other Life Maxims I’ve Borrowed)

“Pet a cat when you encounter one” isn’t likely to be found on your typical list of rules for life. It was, however, in Jordan B. Peterson’s 12 Rules for Life: An Antidote to Chaos.

The natural evolution of reading someone else’s “rules for life” is thinking about your own rules. This mental exercise was prompted even further by reading Nate Green’s “10 Short Sentences I Use To (Basically) Run My Entire Life.”

I’m certainly not self-aggrandizing enough to suggest that I can come up with my own “rules for life.” I don’t believe I’ve experienced enough to come up with my own unique maxims. However, I have developed a habit of stealing from smart people.

So, with that in mind, here are 10 maxims I’ve borrowed from other people and adopted as “rules” of sorts for running my life. They’re like guiding principles that I reflect back on often. Hopefully, they help you in some way. If you ignore the rest, follow rule #10.

Continue reading “Do Hard Things With Good People (and Other Life Maxims I’ve Borrowed)”