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A Letter to Fellow GeneralistsFeatured

The startup world, specifically in tech, is often represented as a place where the money is never ending, the ideas are abundant, and there is always a chance to be part of the next big thing.

As an organized do-er in a sea of visionaries, real and self-imagined, I struggled with identity through most of the first 10 years of my career in the startup community as I never held the same title twice. I was the definition of a generalist (before the role of generalist existed).

I want to help those surviving and thriving in a “what have you done for me lately” startup culture to articulate their value and professional worth as a do-er of all things and master of none.

Embrace yourself for your excellence in chaos

The chaos of unknown outcomes is where I find the most professional (and arguable personal) comfort. I have been a Chief of Staff or generalist in industries ranging from cannabis to fintech to SaaS to, most recently, a non-profit tech bootcamp - chaos is the common denominator.

At this stage of a startup, expertise is desired but often hard to find, nonexistent, or unaffordable. At this stage, chaos is what a company has in abundance and it is what I do incredibly well. Chaos for me has shown up in many forms such as missing or unknown processes, unproven sales or marketing focuses, a lack of human resources or hiring support, and a changing product/company vision as extreme growth provides more insight into the customer’s needs - and those are just a few examples.

Communicate Your Value - Chaos in Practice. When I sit for job interviews, which I have done roughly annually for 10 years, I can say with 100% confidence that I can get your task/company/department/team/project to iteration #1. It will not be perfect. But I know how to ask questions, go find experts, request support, pull in team members, communicate next steps, and give the true experts on your team a jumping off place for building the next (and better) iteration. Perfect is an enemy of good and chaos rarely allows space for more than good enough. As a generalist, you know how to take the victories and the losses, learn, and try again. That is invaluable.

What I hope for you fellow generalist: Thriving in chaos isn’t a universal talent. The ability to see the company for what it is currently AND what it could be AND the path of how to get there is so unique. Visionaries see what the company can be, those that keep us grounded see the company for what it is, and those very experienced in their skill can see their path. You bridge them all. You are the do-er of all things and the master of none. I hope for you that you embrace your ability to embrace the chaos and the full picture.

Know yourself and your patterns. Your patterns are your superpowers.

I THRIVE in companies 0 - 100 employees. Not everyone is built for every stage of a startup lifecycle and the workplace would be a better place if more of us admitted that to ourselves. The moment I embraced that I was most successful working directly with founders in small companies, building and proving concepts, my story both for myself and others became clear. I may never take a company to IPO, but I will be the one who helped to build the foundations and was happy to hand off my role and start again when the company outgrew me.

Communicating the Value - Know Your Patterns and Know What They Are Worth. Being a generalist doesn’t mean you have to be great at all things at all stages of all companies. Being a generalist means you are great at a variety of things and you know how to identify when a company needs you before the company itself knows.

What I hope for you fellow generalists: That you find and not fight your patterns. Trying to be everything to everybody can lead to imposter syndrome, exhaustion, and discontent. Embracing who you are and what you’re great at makes you best in class and focused on roles that will empower you to learn and grow.

Know When to Say No - To Yourself and to Others

Saying No to Yourself - Never compromise your values. In a world where your superpowers can build anything, build something you would never be ashamed to discuss with a group of people you didn’t know.

Saying No to Others - Tell your boss and leaders, no, and do it as often as they need to hear it. You may be the only one with the view and access to give them that information and it’s critical.

Communicating the Value - The Art of Saying No. Executives at all sizes of organizations are surrounded by cheerleaders and “yes” people. That is somewhat by design. As a Chief of Staff or generalist, you don’t have an allegiance to any specific department, project, or task. There is extreme value to any leader in having someone they trust that will disagree, present an alternative point, or tell them no. This doesn’t mean you are destined for constant confrontation - it means the Executive you work for just made their most important hire in someone that isn’t afraid to voice the blindspots and be honest, compassionate, and direct.

What I hope for you fellow generalists: That saying no is what will define your path. Your skill set is so diverse, you don’t have to stay anywhere that doesn’t align with what you want to build in the world. Additionally, you have the influence to help an organization hold itself accountable which is invaluable to the right leader.

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In conclusion, what I hope for you fellow generalists (and managers of generalists) is that you take the time to make a list of your superpowers and give yourself the time and grace to find a role that fits. Know your worth. Know that saying “no” at the right time to the right executive can save a company or company culture and that is a very powerful influence. Most of all, I hope that your list of superpowers helps you understand the value you bring personally and professionally to the organization lucky enough to have you.

@schmitzc love this! "Being a generalist means you are great at a variety of things and you know how to identify when a company needs you before the company itself knows." > Do you have any advice on how to get buy-in from the company when they may not yet know or see the value of the things you're identifying it may need before they do? This is one of my biggest struggles as a fellow generalist. Do you have any specific examples of how you've been able to do this? I find myself at a loss for this all the time.
Hi Aura77,this is where you are going to have to sell your ideas. If they don't initially see what you are seeing they need, you are going to have to back your ideas up with data. Show them why they need it and how it will improve the company when they would implement your idea. How does it fit into their business strategy... what are the key results you idea will lead to...
That’s fine in concept, but data doesn’t always tell the full picture- something a generalist knows very well. Nor is data the only factor that should matter. People are irrational, as much as we like to say we fall back on data. It’s not always the case.Maybe the male leaders can’t see what sense a woman is presenting because he’s sexist and a woman couldn’t ever possibly be right. Maybe the engineer won’t agree with or try to find some fault with the data because the designer presented it and it doesn’t fit his (or her) narrow scope of view. A billion reasons presenting data is only ever half the battle. Generalists are often discounted specifically because they are not the specialist, even though both are valid. So this is my question. How to be heard, as a generalist.
What makes you think I am not a generalist Aura77? ;) If data doesn't tell the complete picture (it hardly ever does) that is where you selling it comes into play. You have to tell them your story, what you see, how you see it helping etc.. the data is for the people who aren't generalists. You need to paint the picture for people and data will make it clear for the people who do want numbers. Don't get me wrong, data can be real data but I am not even talking about that so much, it is mostly key results on what you know how the company will improve.. how much will revenue grow, or how much more people will the company attract/attain etc. Just translate what you see in key results. And I know this works (for me) because that is how I do this...
Speaking as a product manager (a very generalist role in my experience) I think framing can help - I use analogies a lot and when it comes to explaining my value as a generalist, it can be as simple as this:"The specialists are looking at the trees. I'm looking at the woods"- my ability to understand *enough* about different disciplines without being the subject matter expert in any of them allows me to offer a more objective, balanced viewpoint that takes all needs into consideration. It's the same value that many consultants bring - being able to observe the specialists from a step back, and see where the gaps are between them all, where things can be improved etc.When it comes to demonstrating the value of ideas you have, it will depend on the receiver. Some people believe in data, so find comparable examples. Others will follow a good story, so finding a narrative that works can be important. Many, particularly execs, respond well to clear numbers - if we do this, we'll achieve X, and if we don't, we'll lose Y'. Noone likes to take risks or spend money, so can you find ways to test your ideas on a smaller sample, in a low cost way etc to prove out their value? If in doubt, get the specialists on your side - to me, part of the beauty of being a generalist is the number and variety of relationships it allows me to form, and the myriad ways I get to practice influencing others. If only the experts are being heard, bring them with you! Hope there's some helpful thoughts in there x
Thank you so much @aura77 for such great questions and @leilani213 for such great answers/feedback. I agree entirely with the previous responses surrounding finding what matters most to the decision maker or organization. Is it data? It is a strong narrative? Is it the credibility of a subject matter expert? Is it the actions of competition? Is it outside examples of how this idea has been used/done successfully?For example - for those data driven, go straight for economic impact. I have pushed previously for hourly wage increases for a warehouse team during the Covid pandemic when funds were very tight. I approached the suggestion by having analyzed how much the total raises would impact our payroll cost per year. From there, I compared how much had been spent the previous year interviewing and rehiring employees + a competitor analysis on the wages offered in our industry and geographic area. I made the case that the raises were going to save the company money overall as the cost of rehiring was substantially more. It was irrelevant to management that I was also very personally driven by the fact that the raises would benefit our workers by allowing our company to pay above market rate.Additionally, I have made some great cases for change that were not accepted and that's ok too. For me, part of success in being a generalist lies in my ability to represent many different viewpoints or ways for the organization to improve but I don't take the final decisions personally. I am not the CEO/Executive Team. I am doing my best work to make sure the leadership team has a more complete view of the business and its possibilities. I have been right. I have also been wrong. I don't focus on either outcome too much as I will be moving onto the next challenge based on decision that is made.I hope that helps!
I imagine that anyone creating a thread about generalists has read Range. I can't stop thinking about the recurring example in the book about how NASA's culture of 'data is king' led to the tragic loss of the seven Challenger astronauts. How there were those who had hunches and feelings that something bad could happen but didn't feel comfortable putting their jobs on the line bringing up the not-quite-hard-data that fueled these hunches. In tech companies especially, where founding members are often CTOs, it can be SO HARD to get anything that isn't a hard data sell point across to those in charge, in this case leading to tragic consequences. Even if we aren't dealing with life or death on this level, we've all seen how bad decisions can trickle down causing employee burnout, etc etc, things that companies surely don't want.I guess I'm more interested in seeing how generalists can collectively make their/our value known in the way that specialists don't have to do.
Ahh the beautiful imaginary world where generalists are seen as equal value to specialists and not just someone they can pile any and everything on top of without recognition of their indispensable skills. Finding the company (and really that means one person) that appreciates the value of a highly experienced generalist is incredibly rare. And even if you do, your entire career is built on proving your worth every single day in a way that no one else in the company has to. Sticking to your principles and "saying no when it's the best thing for the company" is hardly an option. Even if that might be accepted, it gets so exhausting that you end up being on edge and anxious from constantly reciting imaginary conversations in the shower and in bed at 3am because you have to find a way to tip toe around egos in order to be heard rather than relegated to the 'replaceable intern' category. This is coming from a generalist that has gone from being promoted to CFO (and COO, i.e. everything at once) of an 800 person company to being treated like an assistant fresh out of high school at a fledging 8 person startup - in that order. Neither situation was fair to me and almost all of my experiences have been on either end of that spectrum. My lack of mastery over a specific skill has been simply an excuse to pay me less in either the monetary or respect department - sometimes both. I'm sure some people figure it out, or maybe they just get lucky with the perfect CEO, but it's never a comfortable place to be no matter how much you accept yourself for what you are. Because the truth is, as a generalist, you're made to be a CEO yourself. The best kind because you see the big picture and you understand everyone's value. The real crisis is when specialists think they are CEO material. Their narrow-mindedness trickles down into every facet of the culture and cripples the foundation of the company. A Generalist CEO instinctively is always checking that foundation for cracks and doesn't let their ego get in the way of fixing it before it's too late.
Okay, but what are the generalist jobs? What's the generalist path? OP is talking about being valuable as a Chief of Staff, and other posters are talking about being COOs and whatever. These are all leadership positions. If you're already cut out for leadership (as the claim here seems to be), then what do you do at the bottom? What roles do you get that don't just treat you as a gopher or secretary and that demonstrate that you are move-up-able? And if one more person talks in vague terms about "roles that fit your values," I'll scream. I'm looking for a concrete list of job titles, because clearly I have no idea what's even possible out there.
👏👏👏👏👏Exactly my question as well. I suffered a lot as a more jr level employee because I was interested in all aspects of the business, and didn't understand that my bosses/other sr level people around me just wanted me to "stay in my lane"/"pay my dues".
My experience so far is that no one believes you when you say you're good at a bunch of stuff at once. I did actually like the view of "chaos in practice" that was presented here. Most other treatises praising the generalist seem to want you to feel good about being a stepstool, so this view at least gave the generalist some agency. But so far, if I go into an interview and say "I'm generally good at all aspects of your business, I can see the big picture and get you where you want to go, and I thrive in chaos," they're like "uh huh, sure, the last 20 people said that too. Now let's talk about your specific skills...."
As a generalist myself and a long-time IC, I've found success as an early member of the account management team at a smaller startup. Titles that are being used for that space include account manager, account director, customer experience manager, partner experience manager, customer success manager, and I used my 5+ years on that team to also take the lead on developing onboarding and training programs for new teammates, contribute to employee experience and ERGs, and learn about vendor ecosystems in the benefits space.And then I took that to a data science company as essentially a program specialist and developed program manager competencies. Through self-advocacy, I lined myself up as a team lead and future manager. Unfortunately, layoffs happened, so I'm attempting to regain my footing and advocate for the fact that I thrive in early stages, too, and can help create new programs. That has me looking at Account Director roles in younger companies, as well as Assistant Director roles in traditional education that are newer functions. Roles that fit my values are roles that allow for experimentation and the possibility of growth. It's hard being a generalist, that's for sure, and it's even harder because every company calls what we can do something different and houses it under a different department.
Thanks for the concrete list. :) Most of my career has been in the academic sphere, so I genuinely have no idea what roles companies even have these days, and trying to find good search results for a generic skillset can be tough, so it's good to have a starting point.
Of course! I get it, too--I come from higher education, specifically academic advising, so while my skills transferred, there was a huge learning curve to just the structure of business and all. (And I had minored in business administration and spent time in a corporate setting prior to getting my Master's in Education!) Even for roles like "Data Scientist," those responsibilities look different from company to company. I know folks will say to conduct a job search based on skills or competencies, but for the life of me, I haven't figured out how to do that either.
I guess Project Manager is the best title for a generalist I can think of. It gives you some agency because you own a project; it's not a doormat position. BUT to really be accepted as one, you kind of need the PMP certification. There are some good classes online though to get the gist (I took one on Coursera from University of Virginia like 6 years ago and it was really good). Once you have the framework for the process, your generalist skills fit right into it. Another benefit is you can kind of craft this path yourself because you can just make something at work a "project" and manage it to completion. Then make a bigger one and so on. I have mostly worked in real estate development so the projects there are pretty straightforward: get the thing funded, built, and sold/leased. But I also was director at a medical practice for a while and there I made everything a "project." "Building an Electronic Health Records system and process to meet compliance standards" - was a project, for example.
Thanks! I did actually go down the Product Manager path, which I thought might be similar but for software, but man, that was a whole lot of fighting all the time. Maybe Project Manager is a better way to go. I haven't wanted to commit to PMP before, but something on Coursera sounds like a good idea.
probably differs by company, but i found in software at least, being in product was where i got the most respect, although i had to specialize. Product marketing allowed me to generalize more, but then more people think they know how to do my job better than i do which gets irritating when their suggestions (or stronger) arent based on data
As someone who is a generalist in company operations, HR, and talent - titles that tend to work for me are: Business Operations Manager, Talent & Culture Generalist, Talent Manager, People Operations Generalist, etc. I'll do a search for roles that specifically say "As our first XX at (company)" and even the dreaded "wear many hats" so that I can target those companies for opportunities. Generally I thrive in roles where I start as an IC, build processes and infrastructure, and then hire on 1-3 team members as part of the initial scaling. I do not currently have ambitions to be a VP or C-Suite. As a generalist, I am someone who actually thrives in middle management (???) and in the scrappy building stages. I loathe red tape and overcomplicated processes so have learned 500+ companies just aren't for me. The hardest part is finding those roles for 0-100 companies as a lot of those early hires are referrals and/or aren't featured on your typical big job boards, so the best way to find those opportunities is to network, following early stage companies on Crunchbase, and actively reach out to introduce yourself before they need someone in your role.
Thanks! That's a good list of roles, and great tips.
Wonderful advice! This has also been my path Tori 👏
Thank you SO much for this @schmitzc 🙏🏼It couldn't have been a better time for me to read this. I've recently been laid off and back on the job hunt. I've found it a struggle to market myself because I view myself as a marketing generalist which does give me imposter syndrome, especially with all the specialized job postings out there. I love how you've framed it as a superpower and much needed in the startup space. Also, a good reminder to not comprise my values while I search for the next company to join.
The early stage startup comes packed with challenges and learning that are inimitable. And each one is its own beast. Never forget that the C-Suite are some of the greatest generalists there are. Startup Generalist ask questions others are blind to, and generalists think about the whole (business and culture) when they problem solve.
The question that bugs me most is- since most of us, generalist or specialist, will NOT be C-suite, how can generalists at all other levels be valued to their full potential? Especially junior level employees.
It's absolutely an art to make those achievements translate to new environments. If the board only approved a low salary for the role, I'd negotiate a six-month bump in pay before I ever accepted the role. This set a pattern for pay bumps going forward, where I could more than double my salary in under two years without asking. How would you define valued to full potential at all levels?For me being valued as a junior was being heard, having trust and autonomy, getting the support and resources I need to complete the mission, then having my impact rewarded. But as I've gained experience I realize I almost always lacked mentorship to understand what the next level could be.
Specialists are easily valued because so much about what they do is linear and easy to understand. Generalists are often the ones who connect the dots between specialists. Telling a jr/generalist to stay in their lane can unwittingly prevent important connections from being made. Being valued would mean being given the latitude to operate. Being seen as an integral part of an org even if not working on the hard data stuff- what use is data if you can’t synthesize it into anything meaningful? Data driven skillsets often preclude big picture creative skillsets. To succeed you need both. And yet so many companies will unwittingly shoot themselves in the foot by favoring a specialist’s skills above all else.
To have equal footing and be recognized as someone who can see the forrest and the trees (not to mention weather, seasons, animals, and interwoven flora) avoid organizations with silos of management. Whether you are a generalist or specialist, the executive or founder too in love with their own ideas or authority won't change, and won't advocate. Look for innovative organizations that promote cross departmental and matrix management. Position yourself as the advocate for all (brand, business, stakeholders, shareholders, users, buyers, team, etc.). Back in the day, one of my duties was "morale" without the cool title of Chief Morale Officer. Day before a widely anticipated team potluck, the C-suite told me to cancel. I refused. Their reasoning was garbage. I explained that I'd already accounted for their lack of participation, and if they forced a cancellation they'd lose 10% of the team. They could consider this my experiment. The org potlucks became a huge part of the culture and culture sharing. 15-years later, the team is spread all over (different companies and time zones), but we make time to reconnect. Use logic and reason, even if there isn't hard data to cull. Find ways to document how a customer, client, organization "shot themselves in the foot" and how you'd have prevented it. With some refining, I bet there's a data point or two you can use to demonstrate significance. As a junior employee (and college dropout) I asked the COO for 30-minutes to walk me through a big initiative they'd just announced (with A LOT of fanfare). Out of 50 people I was the only one who kept seeing the Titanic sinking. So I mapped out my thinking into a decision tree. We walked through my questions together. About 8-levels into my decision tree, the COO excused himself to urgently speak with the CEO. The project was terminated immediately, saving 12-weeks of development, and millions of dollars. That's not to say I haven't been disregarded many a time (more so with an MS and decades of experience). Or even caught guff only to have my input claimed as someone else's brilliance later. Every year I rehash the good and the bad to align and connect with those who understand I'm there to do my part, which is heavily unscripted (no lanes to stay in) and yet crucial to success.For job titles, mine are definitely not a linear path. I found a way to make sense of it over time.
Such a great perspective and jumping off point to numerous threads of conversation! One aspect not mentioned is the value of a generalist education AND work experience. Having both has enabled me to pivot and change careers about 4 times in 20-odd years, rather than riding one career track the entire time. I was able to navigate some fairly large life disruptions (major health accident, economic depression, failed startup, etc) to land in a career that has grown my net worth and satisfies my insatiable curiosity, desire for growth and hard problems. Would I be farther ahead if I went the specialist route from education through career? Maybe. But I don't think I would have bounced back as fast from catastrophes or had the depths of resilience if I had stuck to one path from education throughout my career.
Thank you for this post, it's incredibly powerful and really got me thinking. I've also jumped around in my career a lot, sometimes after a year sometimes after just 6 months. The place where I felt the best about myself was very similar to what you are describing. A very early stage startup that needed a generalist who could work on design and development tasks interchangeably and help ideate and brainstorm with the founder on next steps. I loved working directly with the founder and loved being able to build something from the ground up. Unfortunately after 8 months the startup was struggling financially and they had to let me go. Rather than going to another startup I decided to go to a more established company after that, where I wasn't as happy, and then another, and another. I missed the startup environment but I also felt ambivalent about the chaos and insecurity. I often thought about starting my own business but the thought of dealing with finances and marketing, plus not having an idea I felt like I could really stick to for a long period of time, were turn offs. I did write a book about breaking into tech but I didn't have enough social clout to make it go viral. I have a similar issue with my painting which I have had more success in selling but also having to constantly promote and share my work is hard for me. So I guess I thought if I couldn't hack it with writing or art I didn't think I could hack it as a tech entrepreneur either, despite having a lot of the skills to build an app. I'm not unhappy where I am right now exactly but I do feel kind of lost. Like being independent with my own business still seems like a more appealing path than going back to a startup environment, but I like the team I'm on and I feel supported with enough free time to pursue my hobbies. Yet it's still far from the stuff I could imagine the most ambitious/creative version of myself building. I'm not really sure if I have a question from all of this, but appreciate any advice or just a sympathetic ear. Thanks for reading this.
What an absolutely beautiful reflection. Needed this so deeply. Thanks for sharing!
Thank you for this post!I like to work on a project-basis - this can mean "events", or being a tour guide, or a Karaoke DJ at the #1 spot in Las Vegas!For me, being a "generalist" means I understand lots of lots of different people and can work as the "bridge" between the client and the software developers, or the founder and the investor, the writer and the producer (films) etc.
This is incredible advice, thank you for sharing!
Loving this post and this thread! So much to respond to, but want to focus on this:"what I hope for you fellow generalists (and managers of generalists) is that you take the time to make a list of your superpowers and give yourself the time and grace to find a role that fits."I have spent many years attempting to do this. What I have found to be true for me as a result is as follows:1) While some roles may be better fit than others, the concept of having one and only one role is a specialist concept. Having a single role is, by its nature, at odds with how a generalist operates.2) Taking on multiple roles (wearing multiple hats) on an ongoing basis is a good way to get burned out.3) As a generalist, the only role that really makes sense for me is the role I define and actualize for myself. It does not work for me to try and 'find' a role - I have to make one.