Let me give you a pep talk.
Finale/summary of what I wish I'd known before leaving consulting to join a Series B start-up
Goodbye emails are my favorite. If you’ve worked at a big consulting company, chances are you’ve read at least a dozen of these farewell messages. Keywords: bittersweet, grateful, excited, the people. Whether it was an itemized receipt of every project and team they’ve ever been on (“Shout out to crying in the shower and eating hotdogs for every meal in rural New Hampshire, haha”) or a short-and-sweet note, these emails always gave me a pang of hope for my post-consulting prospects. I’d straighten just a little in my scratchy H&M blazer, and think to myself that maybe—just maybe—my liberal arts degree, emotional trauma from always getting the middle seat on 8am flights, and smattering of consulting engagements would mean something to some hiring manager out there.
Some 16 months after leaving, I come bearing good news from the post-consulting afterlife, and I want each of you who follow this newsletter to hear this. Your skillset is valuable. You will find a good new job.
I’d like to reiterate what I mentioned in my very first newsletter, which is that I don’t claim to have a profoundly unique point of view—I’m not the first nor the last to successfully make the transition from consulting to industry, or a start-up, or to product management. None of the advice I have is materially new or groundbreaking. But I’ve shared the key things I would’ve found helpful to hear back when I was about to embark on this time and energy-consuming process. I’d like to move on to tell you more about my experience transitioning to Product Management, but first, I’m gonna summarize each of the last four posts, share some feedback and additional suggestions from the community, and give you some reasons you should feel pretty freaking optimistic about your career journey. Sound good? Alright, let’s do this.
Should you leave consulting and join a start-up?
If you only remember one thing from this article, remember that a start-up gives you a much greater shot at ownership. And by ownership, which is at-risk for becoming another meaningless buzzword, I mean the ability to see something through from idea to execution. In my first role post-consulting, I realized that loosening telehealth restrictions meant that we could get therapists to serve clients across state lines and then stood up a program to double, triple, quadruple the reach of our program over a few weeks. It was exhilarating. My partner left consulting to go to a DTC e-Commerce fashion and eyewear brand: he owns the promotional calendar (e.g., when to offer a discount) and obsessively refreshes Sales on the Shopify app to see that sexy hockey stick every time a promotion goes live.
Feedback I’ve gotten…
“Somewhat missing the obvious here: if you make this type of jump you should be comfortable betting part of your career on a particular startup's success.” - some dude on Reddit
I’d respectfully disagree here. You should most certainly do a shit ton of due diligence on a start-up before you join. You should approach each role with skepticism, and ask yourself whether you would personally invest, say, $10,000 of your own money into this start-up. Because, guess what, that’s pretty much exactly what you’re doing when you accept equity as a meaningful part of your compensation. So, I mean, don’t be an idiot and join a company you don’t fully believe in. Ask whether they’re profitable and/or when they expect to be profitable (scroll down for some great questions around this). Press on what folks think their company’s secret sauce or competitive advantage is (and don’t surprised if they turn the question back on you, since that should be part of why you want to work there).
That said, regardless of whether your start-up becomes a unicorn, it crashes and burns, or—this is the most likely path—it does just… fine, as long as you have a compelling story to tell about your personal impact, you’ll be just fine. This ‘story’ looks different for each person and role, but can include what you had end-to-end ownership over, your growth trajectory and ability to wear multiple hats or up-level quickly as the team or company matured, etc.
Need more convincing? Remember Quibi? The short-form video company making TV shows for your phone? Well, it had raised a cool $2 bill in funding, had big names like Chrissy Teigen and Idris Elba attached, a ton of Hollywood hype and was teeming with tech talent. Well, it shut down six months after launch. And yet? I just did a cursory search for former Quibi employees and they seem to be doing just fine: they’ve landed at LinkedIn, Apple, Cash App, to name a few. So again, it’s the story you’re able to tell that will drive you forward in your career. It’s ideal if you can have both an impressive story and a shiny start-up unicorn brand, but if you had to choose: bank on the story, and be rigorous about finding a role where you can write a great one.
So you've decided to leave consulting. Now what?
If you only remember one thing from this article, remember that you can’t have it all, so identify your top priorities and test for them. I sincerely hope that you find—and get—the job of your dreams that checks every single box. But, in my humble opinion, you’re going to be waiting a long time if you’re holding out for the perfect role that may or may not exist, especially if you’re earlier in your career (e.g., in your twenties). So be clear on what matters to you most, whether that’s brand name / prestige, salary, a crazy growth trajectory, a great manager, or gaining expertise in something specific… the list goes on. When I was leaving consulting, for example, I was looking to test my strategy skills (do I actually have good ideas?) and get some ops chops (can I implement those ideas well?) at a company that was doing things I cared about. I was willing to sacrifice a little on the title and the pay in exchange. My own priority stack continues to shift and yours will too, it’s natural! Now, what’s more important to me is the scope or actual content of my day-to-day work and being at a truly user-centric organization, and I’ve gotten enough experience to the point where I’ve got a firm floor for both title and salary. So when I’m on informational interviews with people, I’m asking questions that help me test whether a role or company truly checks the scope and user-centricity boxes.
Feedback I’ve gotten…
This is an awesome follow up and a super actionable framework! I’ve recently been working my way through a book/exercise called YouMap, which really helps articulate strengths, values and skills. Would highly recommend that as a continuation for folks struggling with the “jack of all trades, master of none” feeling consulting often leaves you with when trying to decide where you want to go in life and career! - Tld44 on Substack
Thanks friend! I haven’t personally read YouMap, but a few books I found helpful for thinking through the priority stack are: Designing Your Life by Stanford Design School professors (summary here) and The Start Up of You by Reid Hoffman (summary here).
Hold up. What about business school?
If you only remember one thing from this article, remember that there are lots of benefits to going to B-school, but do not blindly assume that you need to go in order to have the career you aspire to. There are dozens of very compelling use cases both for going to B-school, and not going to B-school. However, I’d like to challenge the assumption that it’s a pre-requisite for success.
Feedback I’ve gotten… This was a spicy topic, and feedback ranged from super positive to people aiming flame-throwers at me. I got a lot of angry people saying that my post reeks of confirmation bias. I understand their point of view, and maybe that’s what I get for posting in r/MBA, since that obviously caters towards people who are already invested in going to / or are currently in B-school. But one Reddit reader summed up my main point nicely:
It’s amazing the allure the MBA has that makes people turn away from great opportunities to get it. There is no business school on earth that can teach you what you can learn from being part of taking a small firm to being a unicorn.
[…] I’m not being negative. I went to a pretty good school, if you go by ranking and I liked having an adventure and living in a new city and going through recruiting (because I tend to believe hard things are good for you). The world has changed, I think the allure of the degree makes us discount what we can gain from those two years of putting that same level of intensity into our work. - Narrow_Evening_5524 on Reddit
What questions should I ask in the interview process?
If you only remember one thing from this article… optimize for finding a great fit over getting every single job you apply for. I can’t over-emphasize this. Success is finding a job that satisfies your priority stack and allows you to tell a great professional growth story. So if you are shown the door mid-interview process, or you were excited about a role but just not vibing with the team, do not despair, and remind yourself that it clearly wasn’t the right fit. Moreover, having now sat on the other side of the table interviewing candidates, I can say with confidence that there are literally 100 different reasons you might be rejected from a job that have nothing to do with you, such as: 1) there were candidates who applied earlier than you, were further along in the process, and may have already been offered the job; 2) the role was only ever really going to go to an internal candidate but it’s an HR-mandated policy to post the job externally, too; 3) the role has now been consolidated into another one or the scope/focus has materially changed so what they’re looking for has also changed… so don’t, seriously don’t, dwell on the rejection. Ask for feedback (although 80% of the time you’ll get no response or be told that they can’t share feedback) and then move on. Wasn’t a good fit—their loss!
Feedback I’ve gotten…
For a start-up - it takes guts, but I always ask what would cause your start-up to fail. It’s in the same vein of what is one or two things you think the company does super well, and what do you think the company could do better? (I leave it open-ended - it can be to the specific team, processes, or the company as a whole). Really gets to the problems you’ll run into on the job and good to ask across teams. - Product Manager on Fishbowl
I love this question, and will be adding it to my own personal arsenal of questions that are great to ask folks at any stage of the interview process.
Excellent post and appreciate that it's segmented early, mid, and post-offer. Two things I'd add:
Try to get as concrete answers as possible about leading and lagging indicators of [Product-Market] fit (rev growth, unit economics, retention, sales efficiency, engagement, NPS, etc). This is sensitive data but if the numbers are good and they want you badly enough, they may be willing to share.
Once you have your comp package, find someone you trust who can share benchmarks with you. (Investors and some founders/operators have access to comp databases.) Make sure both your cash and equity offers are fair. - Porg11235 on Reddit
Love these! Going back to an earlier point about doing your homework and making sure this start-up is one that you’re enthusiastic about investing in, these are some really good questions to ask in later stages or post-offer. And when you’re at the point of negotiating your offer, don’t be shy about asking friends and friends of friends for start-up compensation benchmarks, and leverage anonymous communities like Blind.
Keep calm and carry on
I had a minor panic attack the night before my new job. I was in a cold sweat laying in my bed as it dawned on me that I hadn’t actually… done anything in consulting. I had created lots of PowerPoint decks. I had done plenty of number-crunching. I’d interviewed a lot of smart people, both from the C-suite and experts in the field (my life goal, by the way, is to amass enough expertise to become a GLG expert: those people make bank for an hour of dropping NDA-approved knowledge on the phone). But… was I really qualified to get in the driver’s seat?
You may very well have the same anxiety that I did before starting your first post-consulting gig. But I must remind you that:
The soft skills that you build in consulting are incredibly valuable in the ‘real world’ and will allow you to add value from Day 1. I’m talking things like setting an agenda before having a meeting with objectives and talking points, and knowing how to tell a compelling story and set crystal-clear context for people across the organization.
Working, as you did, with many different companies offers you a unique vantage point into what keeps different leaders up at night, what the pain points are for organizations of different sizes and scale and across industries, what good (or bad) leadership looks like… you have a much bigger n than someone who has only had a few jobs and only know what they’ve experienced firsthand. That’s a really valuable and unique perspective and you should lean into that.
Lastly, it’s just a job. I know this might come across as glib since this whole newsletter is dedicated to folks who really care about their career—and that describes me, too! I also know that our jobs, especially in the age of COVID, can take up so much of our headspace not only because we spend most of our waking hours at work, but also because there’s just not that much else to do during the week right now. But what keeps me feeling sane, and tethered to my own sense of self and security, is knowing that the average worker holds 10 different jobs before they turn 40. TLDR: you’ll have many jobs. Some you’ll love, some you won’t, but you’ll learn a ton from each role. No one role is going to destroy your value, and your professional life is not a measure of your self-worth. There, I said it. Onto the next.