Should your next hire be a specialist or a generalist?
Person by person, you’re building your startup team. How do you know if your next hire should be a specialist or a generalist?
It’s a common thought that all members of an early-stage startup should be startup generalists “wearing many hats”. However, it’s a fallacy to believe that every member of your team should be a generalist in the early days. Asking your engineers to hand out marketing materials for a guerilla campaign led by your solo growth marketer between code reviews is not an effective operational startup strategy. (We’ve seen this – literally this – happen, to the degradation of team morale and the crumbling of a great product sprint). Rather, a strategic mix of specialists and generalists helps early teams succeed.
Most founders start as generalists simply due to the fact that, with limited resources, founders can’t hire every team member they’d hope to bring their ideas to life. However, even as a founder, not everyone is a great generalist. While it’s possible to improve your skills as a generalist (yes – being a generalist is both an art and a science), many founders simply aren’t effective generalists, especially if their deep domain expertise led them along the founder journey in the first place.
How DO we decide whether a generalist or a specialist should be the next addition to our early-stage team?
Build a network of team members with complementary levels of expertise to achieve milestone stages of growth
Why This Works
The belief that “all early employees should be generalists” can, in practice, diffuse team efforts, especially if everyone is expected to do everything all at once. Fully opaque roles lead to situations where more time is spent deciding who does what instead of “these people have a function, and others are expected to fill in the gaps.” Think of it like a hub and spoke model - the spokes extend your reach, and the hubs tie the spokes together.
Why Do This Now
In the early days of a founding team, it’s likely the founder or a few of the founding team members are acting as the team generalist. Because this role is being filled, even if originally out of necessity, the impulse will be to hire specialists. Without considering a founder proxy - bringing in a generalist counterpart - the team will begin growing with too many specialists and not enough generalists to be the glue when the founder inevitably has to move from working in the business to on the business.
If you have a founding team of domain and functional experts, you can still find yourself hiring an unbalanced team. It’s common to hire by mirroring what works, which means you’ll likely unintentionally continue to add specialists to the team.
Considering which applies to you allows you to intentionally design your team to cover the areas that matter most while ensuring you are all progressing forward together. Further, in the early days, you are in a stage of building. Great generalists are builders and great specialists drive scale. You can’t scale your tower without building the scaffolding first. Specialists may be able to make something great, but it’s more tenuous than if you have generalists building alongside them. The perfect ratio of specialists and generalists creates micro loops of building and scaling that helps teams get to each subsequent stage.
If you're new to How We Do, we'll next break it down like an expert generalist who leverages the tools, rules, and people needed to create effective systems. A great system for building out your team of generalists is as necessary as the generalists themselves. Keep in mind that modern operations involve the art and science of considering your tools, processes, and people, and there is no one-size-fits-all approach. The outputs will be as unique as the inputs.
how We Do: how to determine whether your next hire is a specialist or generalist.
1️⃣ Identify the domain and functional expertise of your existing team (this is what you know).
2️⃣ Determine the greatest pain points and operational gaps required to get to the next stage (this is what you don’t know).
3️⃣Fill the gap by connecting these two (this is what you need).
1️⃣ Expertise of your existing team
There are four key types of expertise to consider: domain, startup, functional, and internal product management.
Domain expertise is key to solving the problem for your customer. This encompasses the systems within your domain that factor into your business success (i.e. my company is a healthcare startup and I’m at the mercy of the complexity of our healthcare systems). Domain expertise can be a blocker to get to the next stage of growth, but not everyone on the team needs to be a domain expert to be an excellent team member. To succeed, it's worth considering how much outside domain expertise you need, as it can bring fresh ideas to the table.
Startup expertise is a form of domain expertise. Managing and working in a startup is unique, so understanding the experience and knowledge required for your next hires is key. (Quick tip! Don’t underestimate those outside of the startup world. You’ll find scrappy, hungry problem-solvers once you give them a chance).
Functional expertise is the experience and knowledge of a certain functional area – marketing, sales, product, etc. This is the most common way of thinking about expertise and will be the easiest to identify. You know what you and your team are capable of, so this should be an exercise in making the implicit explicit.
Internal product management expertise is the experience and knowledge to build effective systems that connect the tools, processes, and people within an organization. This is the background of an expert generalist, a successful founder, or another cross-functional project owner who can get everyone moving in the same direction.
Tools 🛠️
Use a project or database management tool like Trello, Airtable, or Notion when building out each of these key areas. If used with a Kanban format, you’ll visually be able to see where the expertise lies on your team. Are you a team of functional experts or domain experts? This quick view will help you gut-check your analyses.
Rules (Process): 📝
Identify all areas of expertise on your team in the four key categories above. This will show you the total scope of your team’s work.
Review if anyone is routinely stretching outside of their expertise. Identify the specialists needing to pinch hit as generalists often.
Review your tool stack. What else can be outsourced to free up your team for deeper work?
People: 🫶
Review notes from 1:1s, initial interviews, and user manuals to remind yourself of the skills of your team members you might be underutilizing, or not utilizing at all.
Connect with each employee and ask them how they see themselves - this allows you to ensure alignment while also uncovering expertise areas you may have overlooked.
2️⃣ Identify pain points and operational gaps
There’s a difference between pain points and operational gaps. You might know that you need more sales, and you need someone to drive those sales to close contracts quickly. However, you might also recognize that you are painfully unaware of key sales metrics, limiting your ability to effectively analyze your sales processes, which is causing the slowdown.
Tools 🛠️
Create a Slack to Google Sheets, Docs, or Notion Workflow to capture your pain points as indicated below. Any time you feel something that doesn’t sit quite right, send yourself a Slack, to auto-populate a list for you to dig into at another time.
Use your project management tool for this exercise. This is a great way to keep a running list of everything that needs to be done to better understand the gaps that may necessitate hiring. Further, once onboarded, you can auto-assign these areas of focus without needing additional systems.
Rules (Process): 📝
Develop a list of pain points to synthesize what’s keeping you up at night and preventing you from unlocking the next stage of growth. Time-box this to account for recency bias and weekly fluctuations.
Keep an “Ouch” list of all of the points of friction that are holding you back from your written goals. Something like –
We haven’t closed any deals this week.
We don’t have a clear way to track our closing rate.
Slack is a mess, and everyone is losing tasks.
“Kick-off partnerships” has been on the list for two weeks, and we’re not making any progress.
We don’t have a clear sense of whether or not our customers are getting value from this new feature.
Synthesize your pain points into 2 - 3 key areas. What patterns do you see?
Organize a list of key operational gaps inhibiting your growth.
Create a list of all of the tasks required to run your startup.
Put these into traditional functional buckets – marketing, sales, customer support, customer success, product, engineering, data, people, business operations, etc.
Move all tasks associated with areas of growth and opportunity into one new functional bucket titled “Future Hire”.
Analyze the list. Do all fall under a specific function? Or are they cross-functional?
Prioritize the list. What’s most urgent?
Compare the two lists, and create one, prioritized list of 5 key areas of need on a blank page (so it is not clouded with other data). You can feel this list if you start it with, “The most pressing, painful areas of need that are holding us back are”:
People: 🫶
There are different types of generalists that you can consider in reflecting on your pain points and needs. T-shaped generalists are wide in many areas but deep in one. If you recognize in this exercise that all signs point to a singular, functional hire, where there are key processes that still need to be optimized, built, and scaled, a T-shaped generalist marketer, for example, will be able to lead your growth marketing efforts, but will know enough about content and brand marketing to be dangerous. They’ll also likely know a bit about other functions as well to make them a true cross-functional asset. M-shaped generalists are deep in a few key functional areas, which makes them fantastic first-in-seat gap fillers to experiment in a function before your startup is fully formed to develop processes and systems before bringing in greater specialists. As you map out these needs, you’ll see what’s missing and what’s not.
Great generalists are internal product managers – they’re going to know how to build repeatable, scalable processes by connecting both the tools and processes of one function to another function’s tools. Consider how cross-functional these gaps are.
Generalists and specialists fall on a spectrum, and both are vital to the success of your business. Some projects may be best served by a generalist while others may be best served by a specialist. Understanding how to leverage these roles and have these capable hands at your disposal can be the special sauce that further unlocks your growth. Your operational gaps and pain points can be filled by any type of these.
3️⃣ Fill the Gap
Reviewing both lists, what do you see? What’s missing?
If you have an operational gap in one functional area as both a blocker for growth and a key pain point, you likely need a specialist to jump in to make an impact.
Hiring a generalist would have the most significant impact if you have operational gaps in multiple areas, as well as pain points in structure and clarity.
You don’t know what you don’t know. And if you don’t know what you need next – which is common, and completely ok - inserting a generalist will allow you to experiment with your internal product just as you’re doing with your external product.
There are many ways, some effective and some not, to fill your team. Next week we’ve cued up an entire guide on how to gap-fill based on this exercise. These include future-of-work ways to effectively build your early-stage teams.
Take It Up A Level
Using AI to Improve how You Do:
While you’re searching for your next hire, use AI to level up your current team members in advance of that onboarding. Startups don’t always have the luxury of hiring someone exactly when they want so how can you use tools to create more bandwidth and stretch the power of your current team (think: ChatGPT for marketing content, sales outreach emails, job descriptions for talent acquisition, etc)? And if you’re an AI startup and you can use your own tools, you might need less people than you think!
Digging Into More Resources
Range by David Epstein (Book)
The E-Myth by Michael E. Gerber (Book)
Traction by Gino Whitman (Book)
Pioneers, Drivers, Integrators, and Guardians by Suzanne M. Johnson Vickberg and Kim Christfort (Article)
Actually Actionable
Nice article. Now what?
We’ve taken the ideas above and put them into an action plan for you and your team.
Hiring Plan Week Sprint
Deep Work Sessions
Identify team strengths (45 min)
Aggregate pain points (1 hr)
Hiring Profile Meeting
Review pain points and needs with key stakeholders (5 min)
Evaluate team expertise (10 min)
Outline the candidate profile (15 min)
Once you’ve scoped out what your existing team can do, what your team can’t yet accomplish with their expertise or resources, and what’s really holding you back from your goals, you can determine the right new type of team member to add to your efforts. And (as promised before), the ways forward-thinking founders with limited resources and big dreams make them a reality with people who get it and care? More on that next week.
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Writer: Britt