Getting to know your professional colleagues at a personal level is risky. I regularly read advice to avoid it. That’s a reasonable strategy to avoid some of the lows of gainful employment, but it also hamstrings the chance to achieve truly beautiful successes, not to mention it forfeits a potent antidote to loneliness.
So yeah, not only am I going to ignore that advice, I’m doubling down on getting better at being a student of other people. To that end, last week I started reading How to Know a Person, from which I extracted the following list of conversation starters:
Which of your five senses is strongest?
What are you most self-confident about?
What’s working really well in your life?
What is the “no” you keep postponing?
What have you said “yes” to that you no longer really believe in?
What forgiveness are you withholding?
Tell me about a time you adapted to change?
Have you ever been solitary without feeling lonely?
Can you be yourself where you are and still fit in?
What crossroads are you at?
What would you do if you weren’t afraid?
If we meet a year from now, what will we be celebrating?
If the next 5 years is a chapter in your life, what is that chapter about?
What has become clearer to you as you have aged?
What is the best way to grow old?
If you died tonight, what would you regret not doing?
Full credit to David Brooks here, I’m just repeating his excellent ideas. Keep learning, friends!
Last night ChatGPT had a bug. But not your run-of-the-mill problem like increased latency or complete unavailability. No, it went completely off-the-rails: spouting gibberish, repeating itself ad infinitum, and other nonsensical behavior.
Hilarious though some of the outputs were, it was a powerful reminder that AI technologies are still new and mysterious, and definitely require human oversight. While this incident ended up with random output, I can now imagine a whole class of bugs where language model outputs are wrong in all manner of specifically bad ways. Humorous now, but perhaps less so once we give them agency to act on our behalf.
I anticipate the day coming when I ask my personal Scarlett Johansson to book a family vacation to Fiji and it instead sends an email to my mom lambasting her for wearing white after Labor Day and then sells my living room furniture on eBay.
The future’s going to be something else, of that we can be sure.
It may not seem like much, but you never know the lives you touch just by always showing up, even on the days you feel so small. Turns out it all matters after all.
– Derek Webb
Want an easy way to be perceived as good at your job? Set aggressive goals for being responsive across all your communication media, and especially strive to avoid failing to respond or missing messages altogether.
My own personal targets are the following:
Slack / Text: 5 minutes ideally, 1 hour median, never more than 24 hours
Email / Voicemail: 4 hours ideally, 24 hours median, never more than 3 days
Even just an “I got it, will have you a better response by X time” goes a long way (assuming of course that you do indeed follow-up). Liberal use of tools like reminders, snoozed messages, and do-not-disturb / notification settings make this achievable without completely giving up on work/life balance.
I call the approach “radical responsiveness”. In my experience, it’s a simple way to earn trust with colleagues and customers alike. It works across levels and roles, though it’s particularly helpful when being attentive is part of the job, like sales positions, and especially critical for people management. Be the boss that always responds quickly and your team will be imminently thankful.
Of course you won’t be able to meet these objectives 100% of the time, but being known as a responsive person 95% of the time usually means others will assume the best of you for the 5% of time you fail.
Of all the sources of happy birthday messages (which are truly delightful, by the way), one I least expected was a text from the customer service agent at CoveredCA that I worked with to get health insurance after I was laid off nearly 5 years ago, and haven’t interacted with since.
I get that it’s trivially easy for any organization that knows your date of birth to send out such messages, but…
That’s gotta be some kind of automated message, right? Or a mistake? In any case, thanks for “thinking of me” on my special day!
Never pass up an opportunity to express gratefulness, especially in the workplace. In my (almost) 45 years of life, I’ve never heard someone say “You say thanks too much, please tone it down.” Do it often, do it out loud, and do it in front of an audience.
That being said, the object of your expressed gratefulness matters. What you praise is what you encourage to happen more often. But the converse is true too, what you don’t praise you will discourage. And if your praise for a person’s work is disproportionately towards things less important to their job, you may be having the side effect of making them feel they aren’t actually doing a good job with the things that do matter.
Of course, that may literally be true. You may be using praise of the inconsequential as a defense mechanism to avoid hard feedback of what is consequential. Or you may not be. But if your praise quotient is out of alignment, the individual you’re praising will have to guess. And that ambiguity can be disheartening.
I don’t pretend to know everything that’s going on over at OpenAI, nor all the eventual lessons that will come from it, but unlike most tech-elite brouhahas this one might actually matter, as there’s a strong possibility taming artificial intelligence is “the final boss of humanity” (as one of the players in the ongoing saga has said).
Played around some yesterday with ChatGPT’s voice chats, and can totally see how we’re not far from deepening the emotional attachments to our devices. Her has never felt more prescient or likely. It’s mandatory viewing.
So you want to become (or have been told you now are) a technical team lead? Awesome, congratulations! You’re in for an excellent adventure. But if you’re wondering where to begin, and what’s going to change, lucky for you I’ve been there myself, helped several others through this transition, and have captured some lessons you can apply:
First, make sure everyone on the project knows you’re the technical lead. This isn’t about ego or power, it’s about clarity of function and accepting responsibility. With that comes the need to be responsive; availability for conversation is now part of your job.
Next, get to know the team personally and earn their trust though human connection. You cannot be everywhere all the time, so you need people who are comfortable coming to you with challenges both technical and otherwise. If there are folks involved external to your organization this is doubly-important. Identify a go-to person on that external team and engage with them regularly one-on-one.
Get to know the team professionally as well. What are each individual’s strengths and weaknesses? What technical skills do they have, and what parts of the system need those skills applied? What are their communication styles and ways of being motivated? Personalize your approach with everyone; it’s your role to put them where they can thrive, which in turn maximizes collective success.
Have a generalist mindset. Get to debugging level competency across the entire tech stack, no excuses. You don’t need to be the best at everything, in fact you shouldn’t be, but you should know what good looks like so you can ensure it’s happening.
There’s one area, though, where your knowledge should be unrivaled, and that is understanding your customer and the business case you are there to solve. Get familiar with their requirements and deadlines. Stay connected to your stakeholders, listen, ask questions, and then push their objectives down to the people in your charge. Once again, this is especially important if there are subcontractors who have a limited view of the big picture.
Make yourself present in meetings, erring on the side of being overly-present (especially at first). Requirements gathering session? You gotta be there. Sprint planning and backlog grooming? Not optional. But that deep dive on a bug or tricky technical problem? Maybe let your tech experts handle it, or at least have them gather the data and come to you if they run stuck or need a decision.
Speaking of decisions, apply wisdom to the ones you can delegate and ones you cannot. Specifics will vary project to project, but in general the more reversible a decision is, the less important it is you make it. Another rule of thumb: as soon as you know how to do something well, it’s time to teach someone else to do it, while you take up the next challenge no one else is equipped to solve. Fail at security and you fail full stop, so keep your eyes on anything that could jeopardize it.
High level architecture and technology choices will matter more in the long run than anything decided in a code review, so keep your nitpicks to yourself. Speaking of code reviews, their value mostly comes in peer to peer cross-checks. If you think you have to approve every line of code yourself, you’re doing it wrong. Treat your attention like the precious commodity it is.
Your good intentions of ensuring quality code and other deliverables won’t be enough. Establish quality mechanisms: automated linting and security scans. Automated testing. Continuous deployment. These are your eyes and ears, and more important for you to establish and monitor than you building features.
Take failure personally. Things will go wrong; the minute you blame those under your charge, you’ve lost. Instead, turn your gaze inward to what you could have done better. When you hold yourself to the highest standard, it calls others to do the same.
Finally, don’t stop listening and learning. Get feedback, even when it’s hard to hear, and act on it. Also, there’s tons more out there on being a tech lead, go do some searches and read up. Perhaps you’ll even (gasp) find counterpoints to my above arguments. That’s great! Ultimately you’re a technical lead to serve and empower, and that requires judgment on when to follow the rules and when to toss them and do what’s gotta be done, because no job is below you. Be the person who brings the coffee and donuts, orders the pizza, serves the drinks, and cleans the conference room afterwards.
Sound hard? It is. It’s gonna take a different set of skills and a significant amount of time. You’re going to have to let go of some things you’re used to doing and some things you’re good at (and probably enjoy doing) to find that time. But when a team you’ve led accomplishes more than you could ever do on your own it’s a unique kind of reward.
Amazon promotions require “best reasons not to promote” to be documented, both from a manager and from any colleague who provides formal feedback. Arguably it was the most important part of the process, because it demonstrated that input came from individuals who could see the candidate clearly enough to speak honestly about both their strengths and their shortcomings.
When coaching candidates for promotion, I recommended they write their own version of that section, and then we’d review theirs alongside my own. Why? Because if you shy away from your deficiencies, you have no counterargument to them. They’re going to be found out anyways by any competent promotion evaluators, so why not get ahead of the curve.
I don’t pretend this is easy, especially for people who have battled insecurities or have lacked encouraging support throughout their careers. But it’s essential for making meaningful career progress. When advocating for yourself, look your shortcomings straight in the eye.
There isn’t a day that goes by that I don’t miss my Dad, but this week I’ve been particularly reminded of him being the reason I rarely feel insecure in naming my professional weaknesses. What a tremendous gift from a parent, the words “I love you” and “I’m proud of you” spoken aloud, simply and frequently. I must have heard those words hundreds of times. Thousands. So often that their truth got into my bones. I believed him then, and I still do now, even though he’s gone. Thanks Dad.
I’m coming up on six months since I took the CTO job at RIPL. Enough time to meet the team and get settled in, even bring a few tactical benefits that solve immediate needs. But the real work begins now, that of strategic planning that sets us up for long-term success.
Operating in a C-Suite is new to me. I don’t have a point of comparison, but so far it’s been great. Between the three of us we have a well-distributed set of skills and experiences, which means we can lean into our strengths while knowing the others have our blind spots covered. In many ways we’re operating as a coalition of equals more than a hierarchy; of course there’s deference when required, but the level of mutual trust is such that it doesn’t really come up often. And I genuinely enjoy the company (in both senses of the term). Not sure if this is rare or common, but I’m grateful either way.
Perhaps this is how the best leadership teams operate, more like a unified whole than a siloed set of individuals? It’s an idea worth exploring further; the Freakonomics episode Are Two CEOs Better Than One is probably where I’ll start.
A corollary to the above, especially given I’m the oldest person in the group (a fact worthy of its own post), is that finding mentorship from professionals with more experience in my role means that I have to look to sources outside my employer. It’s why I’m trying to build a better professional network through activities like starting 4S Tech, attending CTO Lunches, joining the Rand Leadership Slack, and taking a tech ethics class. I consider these efforts part of my job, because I owe it to my company to develop myself further.
Ending conversations is always a bit awkward, whether it be in-person goodbyes, the “uh, are we done?” Zoom meeting closer, or wondering if an email chain needs a final “Thanks” acknowledgement.
Real-time text-based exchanges are particularly tough. Here’s my question: is an emoji response a sufficient message that “yes I got your message, I’m acknowledging that, but I’m not keen to talk further”? Is the vibe different if I send the emoji as a standalone response vs applying the emoji as a reaction to the last message I received?
Need some help from someone in the know, which probably means someone younger than myself.
