To plot the course of Anjuan Simmons’ engineering career, you need to go back to an unlikely source — “Star Trek: The Next Generation.” “Geordi La Forge, played by the incomparable LeVar Burton, was the Chief Engineer of the Starship Enterprise. Even though it’s science fiction, seeing a Black man responsible for the technology on that ship inspired me. I began to think, ‘Maybe I can be an engineer,’” says Simmons. “It’s partly why I eventually studied electrical engineering and went into software development — representation matters.”
Simmons did take that path, starting out at consulting firms like Accenture and Deloitte before making his way into the world of startups. And even though he has his hands full in his current role as an engineering leader at Help Scout, he’s taken that early lesson about representation to heart. Over the years, Simmons has managed to carve out a robust side hustle as an oft-booked public speaker, while also writing about engineering and leadership concepts on Twitter and his own personal blog. He covers topics from sleep hacks and the future of VR, to managing for neurodiversity — and he’s not afraid to get vulnerable.
Last year, in the wake of Black Lives Matter protests across the country, his Twitter thread about being a Black tech leader struck a chord. “I often quote Sally Ride, who said, ‘You can’t be what you can’t see.’ Since there aren’t a lot of Black people in technology and we’re not often seen on the cover of tech magazines or interviewed on CNBC, that lack of representation can cause us to question, ‘Do I really have a place here?’” he says.
When I present at a conference, I’m usually the only Black man on the list of speakers, and sometimes the only Black man at the event. I’ve gotten on stage all over the world to represent that you do have a place in technology.
Simmons made the leap from the page to the stage back in 2016 at the open source conference OSCON. His first talk was just five minutes long, but he was hooked. He’s since taken center stage all over the world, from Budapest to Bogota, at conferences such as GitHub Universe, LeadDev, and QCon.
Simmons isn’t the only engineering leader with ambitions to take on writing and speaking. Across different roles and career stages, plenty of folks have lofty goals to build up their personal brand — and opportunities are more accessible than ever. Whether it’s joining virtual conference panels or hopping on the more casual Clubhouse stage, public speaking is becoming more commonplace these days. Creators are launching Substack newsletters left and right, and even Twitter is getting into the content monetization game.
But there’s a wide gulf between getting started and stepping onstage. Speaking off the cuff or crafting content that brings something new to the table is tricky. There’s an engineer’s skeptical eye questioning if they have something new to say, and there may also be a hearty dose of guilt. Is it worth carving out the time to commit to these side projects? Is it adding a new dimension to your career, or are you better off learning new frameworks, catching up on Jira tickets, or taking on engineering leadership roles? We’ve had our eye on this topic for a while now, but have found it difficult to share concrete advice. Simmons expertly threads the needle between relatable, approachable advice, paired with tested tactics to get you started.
After more than five years as a public speaker (and longer as a blogger), Simmons has picked up plenty of tips and put together a playbook for those looking to dip their toe into the crowded pool of “thought leadership” and make a splash. In this exclusive interview, he gives us a crash course in starting from the ground-up — from finding unique topics, to crafting your talk track, plus his hard-won lessons on fitting this crucial work into an already jam-packed eng leader schedule. Along the way, he busts some of the most common myths about personal branding, and the potholes that can throw you off course. While most of his tactics center around public speaking, Simmons also dives into developing your blogging and social brand — there’s plenty of savvy tips to take notes on. Let’s dive in.
MYTH #1: PERSONAL BRANDING IS DISTINCT FROM YOUR DAY JOB.
When folks come to Simmons for advice about building up their personal brand — whether through writing, speaking, or both — he’s got a simple nugget of wisdom: You’re probably doing this already. “I write volumes every day — it’s just all in Slack and email. As part of your job, you have to communicate,” he says.
Early in his career, he started to reframe his perception of public speaking. “My first job out of college was at Accenture, and I eventually got promoted to a manager role. By communicating priorities and leading the team through deliverables, I began to understand how critical communication really is on a professional level,” he says.
He was an early Twitter user, spinning up his account in 2007. But when the character limits felt too restrictive, he launched his personal blog. “I didn’t start blogging expecting anyone else to read what I wrote. I started blogging as my backup brain — whether it’s writing about processes that I’ve found useful or remembering events in my life. There have been several times when I’ve gone to do something and realized I’ve already written a blog post about it, rather than starting from scratch,” says Simmons.
“If there’s one question I get asked the most, it’s how I fit public speaking or personal writing into my day job. But I don’t see them as completely separate,” he says. Adding onto his deep commitment to representing Black leaders in tech, Simmons has seen firsthand plenty of other career boosts that are often overlooked. “I’m often asked about the key decisions that guided my career. In my 25 years in software development, deciding to become a writer and speaker is probably the single decision that’s provided outsized benefits,” he says.
Show your work.
To borrow a quote from his aforementioned Twitter thread, Simmons notes that he does his work with a bit of a chip on his shoulder. “I try to be impeccable in how I present myself. Being late to a meeting? No way. Producing sloppy work? Can’t have that. However, carrying this chip is a burden on top of what is already a really hard job,” he says.
One reason I started speaking at tech conferences was to “show my work” and portray the thoughtfulness and deep understanding I have about working in software development as a Black man.
As you look to shift gears in your career, consider how writing or public speaking can help show, not just tell. “You can craft a resume to present almost any story that you want to tell. Speaking at tech events, writing for tech publications, writing from my own personal site — that goes beyond a resume,” says Simmons.
There’s a lot of ground to cover in job interviews — and the clock is ticking. He thinks back on several times where he’s prepped for an interview — researched the company and the panel, and crafted his key stories — only to sit down with an interviewer who’s seen one of his talks.
“Any interviewer who reads my blog or checks out a video of my talks gets a really solid look at what I do and what I’m really passionate about. We can mostly skip over that discovery piece and just get into the real meat of the interview,” says Simmons. “Does that help me get the job? No one’s ever said that explicitly. I’m sure public speaking isn’t enough by itself, but it helps. What better testimony for my fitness to fulfill a role than demonstrating communication skills and talking about technical topics and engineering leadership onstage?” he says.
Scale your brainpower.
“Just like my personal blog is my backup brain, it’s also a good automatic responder. As an engineering leader, I often get requests from people to help them understand some concept. I used to write a fresh response to each question, but I soon realized that this didn’t scale very well,” he says. “Now when I get a request for something, if I haven’t already written about it, I’ll spin something up and send it to the requestor — and even better, I can then re-share that blog post for any subsequent requests.”
Upskill with free training.
A lot of folks have plans to attend conferences every year, but calendars fill up and some never get around to blocking the time on the calendar. When Simmons signs on to join a conference, most come with a free ticket to the event — and time permitting, he makes the most of it. “By signing up as a speaker, I’ve attended some incredible events that I otherwise would have missed out on. I get to learn about technologies from the people who either wrote the technology or the people who are using it well, then I can take that back to my team — I’ve gotten so many ideas that I can bring back to my boss,” he says. “For example, I attended a conference where an engineer at Yelp discussed how they use a sponsorship spreadsheet to document the ways each engineer is supported at their company. I loved the idea and presented it to my boss, and she empowered me to implement the same at Help Scout.”
Cast a wider recruiting net.
Like most leaders, one of Simmons’ most critical directives is recruiting for his teams. But standing out amidst an endless scroll of job postings can seem like you’re stuck on a treadmill without an off switch. “When I’m at a conference, I’ve always got my hiring manager hat on. I get to meet all sorts of people who are looking for new opportunities, and I’ve placed roles based on people I’ve met. It’s increased my pipeline tremendously,” he says. In today’s virtual conference world, he leans on digital tools — plenty of conferences have spun up Slack channels (and even have channels dedicated to job seekers) so attendees can communicate without face-to-face meet-ups.
My writing and public speaking have made me a better leader because it holds me accountable. I’m on the record saying “This is what I care about.”
MYTH #2: THE BEST SPEAKERS ARE MASTERS OF SEVERAL DOMAINS.
Simmons is a prolific tech speaker, but what most stands out about his side hustle isn’t just the volume of events, but the creative spin he brings to the stage whenever he queues up his slides. He’s connected the dots between technical leadership and the Underground Railroad, centered developers within the hero’s journey, and even teamed up with his wife, Dr. Aneika Simmons, to get tactical about burning down burnout.
There’s an endless sea of topics that you can cover when you step into the spotlight and start clicking through your slides — finding the right one can feel like plucking a particular grain of sand from the beach. One area Simmons has seen rookie speakers get stuck is the pressure to cover a whole slew of topics — which seems especially overwhelming when you’re just getting started building a personal brand. His advice? Keep polishing your best idea, don’t continue trying to mine for brand-new gems. “I’m a firm believer in recycling talks. One of my most popular talks is called Lending Privilege, and I’ve given it countless times,” he says.
Think of your favorite song. Do you ever get tired of hearing that song? It’s the same with a strong talk.
When it comes to pinning down your signature topic, Simmons walks us through a couple of key questions to find your sweet spot:
When you were starting your career, what were the things that you struggled the most to understand? “Basically any answer to this question is a great talk, because every day someone is entering this industry just like you, and they’re struggling with the exact same things. What slowed you down? Some of my early technical talks were about setting up a stable development environment, ways to solve or debug common development problems, or how to write pull requests. These are nuts and bolts topics, but they’re still incredibly powerful, especially for people newer to software development.”
Are there speakers in your field who you look up to? What do you think makes this speaker so great? “My goal here is not to have them copy/paste that person, but to deconstruct the core elements and then bake those elements into their own style. Some of the speakers I look up to are Lara Hogan, Erica Stanley, Saron Yitbarek, and Patrick Kua (just to name a few) because they talk about problems that I encounter every day and can clearly (and often cleverly) explain actionable solutions that I can implement right away.”
Developing a talk: Make it Factual, Make it Friendly, Make it Funny (and repeat).
But narrowing in on a topic, whether you’re delivering a 10-minute breakout session or an hour-long keynote, is just the tip of the iceberg. To combat the intimidating challenge of filling an empty Keynote deck, Simmons tweaks a simple engineering motto and applies it to crafting a sharp talk track.
“‘Make it work, make it right, make it fast’ is a maxim for building software (often attributed to Kent Beck). It basically says that software development should focus on a working implementation of each feature (without worrying about elegance), then improving the code (refactor, eliminate code smells, etc.), then making the code performant. It’s meant to reduce the delays caused by spending too much time upfront thinking through all the ways the feature can be implemented,” says Simmons.
Here’s how he applies a similar ethos to crafting a new presentation: Make it factual, make it friendly, make it funny. He further sketches out each step in the trio.
Make it factual.
“First, I start with the facts of the talk. What are the objectives that I need to convey to the audience? Of course, every talk needs to be based on facts, with sufficient supporting material and not just anecdotes or Wikipedia research,” says Simmons. But of equal importance is tailoring the talk to the facts that concern your particular audience. “You should always touch base with conference organizers — they should be able to tell you the profile of the audience. Another source for research is trade associations. Visit their websites and subscribe to their newsletters to better understand the topics that are top-of-mind for event attendees,” says Simmons.
“One of my most popular talks, Lending Privilege, centers around inclusion and diversity. I cover some heavy topics in the talk like detailed examples of how certain identities have been historically denied access to careers in software development. Some events are ready for a deep examination of this history, while others are not. One way I find out is by doing my research. I then add or remove detail based on what I find,” he says.
Make it friendly.
“With the facts in place, what can I do to make it approachable to folks? That’s where you’ll see me bring in analogies like the Underground Railroad — it’s a thing most people already understand and can connect with. Most conference attendees already have a full-time job — I don’t want my talk to feel like a part-time job for them,” says Simmons. When it comes to constructing the session for easy consumption, he relies heavily on images to make up his slides — because we’ve all felt our eyes glaze over at the first sight of a text-heavy presentation.
“Software engineers love deeply technical presentations, but every developer is also a human, and humans have a natural affinity for stories. I usually weave two or three stories through my talks. Bonus points if I can use stories from my life to connect with audiences — especially when I’ve made mistakes and learned from them,” says Simmons.
“For example, in my Leadership Lessons from the Agile Manifesto, I share how I initially brushed off a Muslim member of my team who was offended when someone on the leadership team made an off-color joke about a pig in a Slack channel. But upon reflection, I realized that I needed to reinforce a culture of respect in every form of communication at the company, including Slack,” says Simmons. “I pinned a message to that channel that referenced the company’s values around respect and inclusion. I wish I had acted sooner, but that small action moved the needle to make the work environment psychologically safer for everyone.”
By the very nature of stepping on the stage, you may feel you need to have all the answers. But according to Simmons, you’re missing an opportunity to connect on a deeper level with the audience. “People are attracted to vulnerability because we all have weaknesses, but few people discuss their failures. I know I’ve been successful in addressing the attendees’ pain points when I see folks in the audience vigorously nodding their heads. That’s the key to getting them to accept my solutions as viable answers to their problems,” he says.
The final ingredient to an approachable talk? Passion. “No matter what the topic is, if the speaker isn’t excited about the conversation, the audience won’t care about the topic. By showing my own passion, the audience can relax and at least watch one person having a good time,” he says.
Make it funny.
“Finally, I always add in the humor last because this takes the most work. As I’m rehearsing I’ll try to find opportunities where I can sprinkle in some laughs — often it takes several rehearsals,” says Simmons. “The whole talk shouldn’t be a comedy set, but humor keeps the audience engaged. I try to catch them off guard with a joke at the beginning and inject some energy in the room.”
He borrows a few pointers from the stand-up world:
Get personal. “I often find the best opportunities for humor are in the situations from my life that I use to illustrate points and get vulnerable. You’ve got to be able to laugh at yourself. For example, I often give my Managing the Burnout Burndown talk with my wife who has a Ph.D. in business. When I’m done with the intro, I hand it off to my wife to present the next section, and I let the audience know that they’re about to hear from a professional instead of someone like me who just gets information from Wikipedia.”
Each audience is different. “I’ve learned that jokes may work with some audiences but fail with others. I have a slide in my Leadership Lessons from the Agile Manifesto that shows the people who wrote the Agile Manifesto back in February 2001 at a ski resort, and it’s a picture of all white men. I say that they gathered at the lodge to have fun, relax and obviously talk about diversity and inclusion. This joke prompts rapturous laughter from most audiences — but it’s also been met with crickets. Just because a joke falls flat once doesn’t mean you should remove it from your talk entirely.”
Lather, rinse, repeat.
This process isn’t one-and-done — it’s an ongoing routine. “Remember that no talk is really finished. Lending Privilege is my most popular presentation, and almost every time I get onstage I end up tweaking something,” says Simmons. “Since it discusses diversity and inclusion as justice work, I often include a recent example of injustice in the news. Whether it’s an unarmed person being killed or the revelation of harassment by a powerful person, unfortunately, I never lack a new illustration of how certain identities are marginalized and oppressed. After George Floyd was killed in May 2020, I often referred to his death when delivering Lending Privilege in the following months.”
It all goes back to putting your stake in the ground with a few cornerstone topics, rather than trying to cover a wide berth. Not only do you focus your attention on your best ideas, but as an added bonus, you’re more likely to get booked. “There are few things more compelling to event organizers than a battle-tested talk. This is especially true if you can show positive feedback from the attendees on Twitter,” he says.
MYTH #3: GREAT SPEAKERS ARE EFFORTLESS.
Perhaps one of the most persistent speaking myths is that you’re either a natural public speaker, or you’re not. And it’s easy to see why this belief has stuck around — the best public speakers always make it feel effortless to the audience. But Simmons is proof that while there may be a select few who easily command a jam-packed room, more often than not it’s an uphill journey.
“I had a childhood stutter. If you had told me in middle school that part of my livelihood would be getting up on stage and talking to hundreds of people, I would have called you crazy,” says Simmons. As he describes it, getting comfortable on stage involved a strange elective choice for a self-proclaimed nerdy high schooler who loved the hard sciences — theater. “I was really keen to not let my stutter hold me back — I did not want my speech impediment to be something that would make me fearful or not realize my potential,” he says.
He admits that it’s advice that’s perhaps a bit cliche, but critical nonetheless — one of the best ways to tackle that fear is to practice. “You don’t have to start in a big room or virtual group of strangers. It can be as simple as volunteering to present a couple of slides in your next team meeting. Build from there,” says Simmons.
For me, it’s been a slow, organic build of getting more comfortable on stage. Be patient.
The greatest professional athletes don’t step out to compete and just wing it. Each is armed with their own set of pre-game rituals — and Simmons is no exception. He’s got tons of tactical tips for setting yourself up for success and nailing it once you’re (finally) onstage.
The night before.
Scope out the lay of the land. “I try to visit the room where I’ll be speaking and get a feel for the layout. By checking out the room in advance, I don’t have to acclimate on-the-fly while I’m giving a talk. These days for virtual presentations, I do a test run with the background I’ll use day-of to ensure everything looks professional and there’s nothing distracting behind me.”
Eat well and avoid alcohol. “For dinner, I stick to ‘safe foods.’ What’s safe to eat varies from person to person, but I avoid carbohydrates and sugar since consuming them makes me feel lethargic the next day. I drink a lot of water and avoid alcohol — which seems tempting if you’ve got the pre-show jitters. But it affects my sleep quality and the last thing I want is a hangover on stage.”
Get a good night’s sleep. “I can’t stress enough how important it is to get enough rest — even if you’re having a blast at the conference happy hour, or have tons going on at home on the eve of a virtual conference. Standing in front of an audience is hard enough — brain fog makes it so much harder. I try to add an extra hour of sleep the night before I give a talk, so if I normally sleep seven hours, I try to squeeze in eight.”
One hour before.
Check in with your tech. “Your exact needs will vary depending on if you’re in person or virtually presenting. In person, I work with the audio-visual person to get my mic attached, do one final check to make sure my laptop connects to the screen where the audience will see my visual aids, and test the clicker I use to advance my slides. For virtual presentations, you’ll want to confirm the screenshare software you’re using is working correctly, that you can see your speaker notes, and that you don’t have any crazy filters set up. The final step is always activating Do Not Disturb on my laptop so I don’t get distracted by errant Slack pings.”
Turn on some tunes. “I pop in some headphones and turn up the volume on my pre-pump playlist, with a closely-guarded set of hype songs.”
Final confirmation. “In person, I confirm the side of the stage I’m supposed to use for my entrance and if the audio-visual person will handle muting my mic or if I need to do it myself. If there’s a timer, I confirm if it will count up or count down, and I usually arrange for someone to give me a five-minute warning hand signal. The same goes for virtual — what are the cues I should expect to keep me on track? These things might seem minor, but any surprise when the spotlight’s on can throw you off.”
Cover your bases. “I avoid food and only drink beverages during this hour, ideally water and no carbonated drinks. I make one last trip to the bathroom (after making sure my mic is muted) and swallow a few throat lozenges to prevent any throat irritation.”
Once you’re on stage.
You had me at hello. “The opening lines when you start your presentation are often the hardest, but they start the relationship you’re building with the audience. My opening lines are the ones I rehearse the most, and I make sure I can deliver them from memory. When you nail those first couple lines, you start to shake off some of the inevitable butterflies in your stomach.”
Sail through any mishaps. “If there are any technical difficulties, they’ll likely pop up at the beginning. When you memorize your opening lines you can deliver them while you or a technician work to fix the problem, rather than feeling like a deer in the headlights.”
Make connections. “It’s critical to make eye contact with the audience — both so they feel engaged, and so you feel connected to them in return. I make sure to scan from the left side of the audience to the right side, and make eye contact with a person in each section (left, center, and right) and speak directly to them for a few seconds. For virtual presenting, every so often make sure you’re looking directly at the camera — not just at your slides or speaker notes. ”
Don’t take it personally. “If you’re giving a talk to an audience of any size, there’s a high probability that one or more people will walk out. Don’t let this get to you. People walk out or log off Zoom for a variety of reasons — going to the bathroom, to hop on a work call, or they realize that another session is a better fit for them. It means the right people are in the audience for what you have to say.”
With a jam-packed schedule as an engineering leader, Simmons admits that he can’t always follow this pre-speaking routine to a T. “I’m not a full-time public speaker, though some people think that. My full-time job is leading software development teams,” he says. “I’ve been on work calls right before I have to go on stage, ran to the stage, gave my talk all relaxed like I just woke up from a nice nap, and then dashed back to the hotel to get on my next call.”
It hasn’t always been easy, but one reason that I speak is so more people like me find a way into tech because there are so many valuable perspectives that we can bring to this industry. Tech will benefit from others coming in and being able to shine.
WRAPPING UP: HOW TO BAKE PERSONAL BRANDING INTO THE COMPANY CULTURE.
At this stage in his career, public speaking is now a cornerstone of Simmons’ personal brand as an engineering leader. But that wasn’t always the case. “I’ve been at companies before that weren’t super supportive of the public speaking, so I wouldn’t be very vocal about it. I’ve met folks who have been told by their company leadership that they can’t do any public events,” he says.
In his view, it’s a huge missed opportunity — especially for startups. “Over the past five years, most companies I’ve worked at were very small. But I’m on the speaker list next to people who work at FAANG companies — it lends credibility to be out there flying your startup’s flag,” says Simmons.
His advice for company leaders looking to bake this into the culture? Be vocal and proud. “Just get it on the record — say out loud, ‘We really welcome speaking and thought leadership and we encourage you to spend time presenting at tech events,” says Simmons. Even better if the company leadership models the behavior themselves by taking the stage. “One of our mottos at Help Scout is Constant and Neverending Improvement (CANI), and that includes getting incrementally better at the craft of public speaking. We have a Slack channel where we’ll post when someone on the team is doing any public speaking and give them a shoutout. By visibly supporting it, your company can cultivate an atmosphere where people feel comfortable saying, ‘You know what? I’m going to dip my toe in the public speaking circuit, too.’”
This article first appeared in review.firstround.com