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“Our current work system has been built for specialists. You have a specific task, you’re in charge of that task and when you leave, your replacement will have done that exact task before somewhere else. It’s a remnant of the Industrial Revolution,” says Milly Tamati, founder of Generalist World, a platform that helps startups and high-growth companies hire and retain generalist talent. “The issue is growing companies need talent that can work cross-functionally, piece things together, make decisions, pivot and jump in wherever needed. That is a generalist.”
Here, Milly shares her top tips to help startups hire generalist talent.
Map out where generalists need to build value
Where does your company need support? You need to have a clear idea of where this person will have the most impact. What problems need connecting rather than deeper expertise? Which teams need better synthesis and coordination?
To do this, you might want to carry out an overview of the company, like your internal communication flows, your recurring friction points and a list of problems that bounce between teams without a resolution — are there areas where specialists are working in silos and creating bottlenecks?
Identify the right mix of skills for your needs
You’re not going to find unicorns who know everything. Some skills you might want a generalist to have could be:
- Skill stacks rather than skill lists. Can they show evidence of connecting seemingly unrelated problems?
- Ability and speed to learn, over specific experience. Look for evidence of where they’ve done this in the past. During the hiring process, you want to hear them reference failures and learnings. For example, "We tried to do X first, it broke at scale, so we rebuilt it using Y...I know the first version failed because..." This shows analysis as well. Or maybe they say, "I knew nothing about this thing, so I did this and that to learn it in three weeks so we could launch."
- Pattern recognition and ability to synthesise information. Have they got any evidence of creating solutions by combining existing ideas?
Prepare well for interviews
As a hiring manager, you need to know what to ask generalists and what answers to look for. Especially as CVs aren’t likely to make traditional sense — this is the magic. Instead, you want to:
1. Test their problem-solving skills. You can give them scenarios to walk you through, like:
- We just lost a key client. Walk me through your first 48 hours after.
- We have great ideas but slow execution. Map out how you'd diagnose this.
- Our engineering and product teams are misaligned on priorities. Walk me through your first week investigating this.
2. Assess their practical skills. Ask questions like:
- Can you walk me through a time you bridged product vision and technical constraints?
- How have you helped non-technical stakeholders understand technical debt?
- Can you tell me about a time you had to choose between speed and quality?
3. Evaluate their growth impact. Some examples include:
- Tell me about a growth experiment you ran from idea to analysis.
- Tell me about a process you built that scaled well beyond your time.
- How have you evolved documentation as a company grew?
Keep an eye out for red flags during the interview
Ones to look out for include:
- They can’t explain their impact with metrics and speak to specific examples.
- They only operate with clear direction or believe things are outside their remit.
- They show no evidence of learning from failure and blame others.
- They have a pattern of creating short-term solutions.
- They focus only on technical solutions to business problems.
Don’t just post jobs on LinkedIn
The best talent often needs to be reached out to. Look for them in cross-functional roles like product ops, growth teams and strategic projects. You will also want to look within fast-growing startups or companies that underwent rapid transformation. Look for early employees and others who've worn multiple hats. Or those who’ve built internal tools, systems or side projects.
Don’t overlook ex-founders — they’ve done a lot. You can also approach communities like Generalist World or other career-focused communities focused on specific verticals for hyper-relevant talent pools.
Give them the correct scope
It’s pointless hiring a generalist but then making them operate like a specialist. You want to ensure they’re set up for success by giving them explicit permission to work across boundaries — and, on the flip side, leadership needs to be aware and bought in that a generalist is going to be working cross-functionally; it’s your job to set expectations with the team about their role. To measure success, create clear impact measurement systems. Reward them for their impact across functions, not just in one area. Similarly, you can link bonuses to system improvements, not just individual metrics.
On the subject of… hiring generalists
1. Are you a generalist? Take this quiz created by an organisational psychologist for Generalist World.
2. T-shaped talent. Where do those who have generally broad experience with deep expertise in a specific function fit in?
3. Are you trying to innovate? You need to bring in the generalists.
4. On our reading list: do generalists triumph in a specialised world?
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