Small Biz Leader · March 30, 2026
Small Biz Leader · March 30, 2026
Choosing the right person to lead a team for the first time can make or break small business operations. This article brings together proven strategies and expert insights to help business owners identify which high performers are truly ready to step into leadership roles. The guidance covers sixteen distinct leadership qualities that separate effective team leads from strong individual contributors.
Brittney Simpson · Vaibhav Kakkar · Mike Zima · Shehar Yar · Dhari Alabdulhadi · Ross Albers · Joshua Schirard · Derek Pankaew · Joe Spisak · Mike Fullam · Scott Brown · Enrico Westrup · Hrishikesh Roy · Nicolas Morvan · Stephen Doran · Emma SansomBrittney SimpsonFounder & HR Consultant · Savvy HR Partner
The signal I look for before recommending a first promotion has nothing to do with tenure and everything to do with behavior that is already happening without the title.
The strongest indicator that a promotion will work is that the person is already doing the job informally. They are the one their peers bring questions to before they escalate to a manager. They are the one who notices when something is off and says something instead of waiting for someone else to handle it. They are the one who treats the team's outcome as personally as they treat their own work. That is not a candidate for a lead role. That is someone already functioning in one without the authority or compensation to match.
What I guide organizations to watch for specifically is how someone handles a moment when things go sideways. Not how they perform when everything is running smoothly. Anyone can lead in calm water. The tell is whether this person steadies the room or adds to the noise when a deadline slips, a client escalates, or a team member drops the ball. Composure under pressure is a leadership signal that no skills assessment will surface.
The transition piece is where most promotions quietly fail. The newly promoted lead is handed new responsibilities without having old ones redistributed. Delivery slows. The person gets stretched past their capacity and leadership concludes the promotion was premature when the real problem was poor transition planning.
Promote the behavior you have already observed. Transfer the workload before you transfer the title. And give the new lead a manager who will invest in them the same way you are asking them to invest in others.
The best promotions should feel inevitable not surprising.
In the early stages of growth, delivery speed can sometimes mask leadership gaps. I promoted the first lead when I saw someone manage both energy and expectations, not just tasks. The biggest sign was how they ran meetings. They arrived with an agenda, ended with owners and next steps, and followed up in writing within an hour.
This discipline created momentum and helped reduce confusion across time zones. When a person can turn conversations into decisions, they can shift responsibilities without causing bottlenecks. That is when you know the promotion will work. The team spends less time clarifying and more time executing.
Mike ZimaChief Marketing Officer · Zima Media
I choose the first team member to promote when they clearly surpass others in domain expertise and consistently use data to drive decisions. To shift responsibilities without slowing delivery, I hand over ownership of that domain while ensuring alignment with overall business goals and encouraging a test-and-learn approach. One clear signal that the promotion would work was when the person repeatedly won debates with data and then iterated quickly on tests to improve outcomes. That mix of expertise, data-driven judgment, and rapid iteration showed they could lead without disrupting momentum.
Shehar YarCEO · Software House
The signal I looked for when choosing our first team lead at Software House was not technical excellence. It was whether the person naturally invested time in making others better without being asked to do so.
We had two strong candidates. One was our most productive developer who consistently shipped the highest volume of features. The other was slightly less prolific individually but spent significant time reviewing others' code thoughtfully, writing documentation that the whole team referenced, and pairing with junior developers who were struggling with complex problems.
I chose the second person, and the signal that convinced me was something I noticed over three months of observation. When a junior developer submitted a pull request with significant issues, the first candidate would reject it with brief comments and move on. The second candidate would reject it but then schedule a 30-minute pairing session to walk through the problems and teach the underlying concepts. He was multiplying the team's capability rather than just maximizing his own output.
To shift responsibilities without slowing delivery, I structured the transition over six weeks rather than doing an overnight role change. During weeks one and two, the new lead continued his normal development work but started attending project planning meetings with me to understand the management perspective. Weeks three and four, he took over code review ownership and sprint planning while I reduced his individual feature assignments by 40 percent. Weeks five and six, he was fully in the lead role with me as backup.
The key to maintaining delivery speed was being transparent with clients about the transition. I told them we were strengthening our team structure and that their projects would benefit from having a dedicated technical lead overseeing quality. No client pushed back because we framed it as an improvement to their service.
Dhari AlabdulhadiCTO and Founder · Ubuy Peru
When promoting our first team member into a lead role, I prioritize consistent ownership of outcomes over raw output volume. I select someone who has voluntarily resolved cross-functional blockers for the team at least 3 times in the prior quarter, as this predicts their ability to coordinate without micromanagement. Gallup research shows teams with proactive problem-solvers in leads see 21% higher profitability, while Harvard Business Review data indicates internal promotions boost retention by 30% when paired with clear responsibility shifts.
To avoid slowing delivery, I reassign their tasks via a 30-day handover sprint, overlapping with their new mentoring duties on 20% of projects. This maintains velocity, as McKinsey stats reveal structured transitions cut productivity dips by 40%. One key signal was their unprompted peer feedback aggregation during a crunch, improving sprint velocity by 15%; post-promotion, this scaled team-wide, validating success as delivery hit 98% on-time targets. This approach ensures seamless growth.
Ross AlbersFounder & CEO · Albers & Associates
The key to promoting someone is to find someone that you can trust to get the best out of others. You want someone who has had success on their own and who can help their teammates succeed when they delegate. One way that can help you figure out whether someone can do this is to have them create a "playbook." Have the person you're considering promoting create a "playbook" for their current role with the company. This would involve documenting their best practices and basically creating an instruction manual for the person who will take over their current role if they're promoted. This helps in two ways. First, it helps to prove that the promotion candidate has what it takes to pass on valuable knowledge to others that can enable them to thrive. Second, it ensures that whoever takes over for the person who is promoted won't miss a beat or slow down delivery when they move into their new role. As far as figuring out if the person you promote will be successful in their new role, while there's no definitive way to tell this, an excellent indicator is if they are natural problem solvers. If someone is proactive about solving problems and good at it, they are probably going to be great in whatever role they take on. To find your team's proactive problem solvers, keep an eye out for the members on your team who don't just bring you problems, but also bring you solutions that they are prepared to implement.
Joshua SchirardDirector · Byrna
The honest answer is I watched how someone handled a moment when things went sideways.
When I was building Byrna's Law Enforcement Division from scratch, I needed to identify who could carry weight without me standing next to them. In SWAT, we had a saying: you don't find out what someone is made of during training, you find out during the crisis. Business is the same way.
The signal I looked for was how someone communicated bad news. Not good news, bad news. Anyone can report a win. The person worth promoting is the one who walks in, tells you a shipment is late or a client is frustrated, and already has two solutions ready before you can ask. That person isn't waiting to be led. They're already leading.
When I found that person at Byrna, the transition was clean because I had been quietly delegating real decisions to them for months before the title changed. By the time we made it official, the team had already adjusted naturally. There was no disruption because the authority had already shifted in practice.
The promotion was just paperwork. The real decision happened six months earlier in a tough conversation they handled without flinching.
Derek PankaewCEO & Founder · Listening.com
The first lead promotion is scary because you're not just changing someone's title — you're changing the speed of the whole team.
Early on, I made the classic mistake: I assumed the best individual contributor should become the lead. Highest output. Cleanest work. Most reliable.
What I learned is that delivery can actually slow down if you promote your fastest executor.
The signal I look for now is something different. I watch for who reduces coordination friction without being asked.
There was one team member who wasn't the loudest or even the most technically advanced. But in meetings, when things got vague, they'd summarize: "Okay, so we're deciding between A and B. If we pick A, that affects X. If we pick B, it affects Y. Which constraint matters more?" That habit alone saved hours.
Another signal: they'd spot misalignment before it turned into drama. Not by escalating — but by clarifying. A quick message like, "I think we're optimizing for different outcomes here. Can we align before we build this?"
That's leadership in disguise.
When we promoted that person, I didn't remove all their execution work overnight. That's another common mistake — stripping someone of what they're good at too quickly. Instead, we gradually shifted ownership of decision-making and communication first, not just task assignment.
The outcome? Delivery didn't slow down. It got smoother. Fewer reworks. Fewer half-built features. Less silent confusion.
The unexpected lesson for me was this: the first lead shouldn't be the person who produces the most. It should be the person who makes everyone else's production more coherent.
Joe SpisakCEO · Fulfill.com
I promoted the wrong person first and nearly killed our fulfillment operation.
When we were scaling past $3M ARR, I needed a warehouse lead desperately. I picked Marcus because he was my fastest picker, consistently hitting 180 units per hour when the team average was 120. Made perfect sense, right? Wrong. Two weeks in, our error rate jumped 40% and three veteran employees quit. Marcus was phenomenal at his own work but had zero interest in helping others improve. He'd get frustrated when someone asked questions and just do their work himself to "save time."
The real winner was sitting right there. Sarah picked 140 units per hour, not the fastest, but I kept noticing something. During breaks, people clustered around her. When new hires looked confused, they'd wait for Sarah instead of asking a supervisor. She had this way of explaining our bin system using sports analogies that somehow made everything click.
Here's the signal I learned to look for: Who do people naturally ask for help when management isn't watching? That's your leader. Not the highest performer. Not the person who's been there longest. The one the team already chose before you did.
When I promoted Sarah, I did something counterintuitive. I pulled her off the floor completely for her first week as lead. No picking, no packing, just shadowing problems and learning our systems from the management side. My ops manager thought I was insane because we lost our second-best picker during peak season. But that investment paid off immediately. Sarah restructured our training process and our new hire ramp time dropped from six weeks to three.
The mistake most founders make is promoting someone into leadership while expecting them to keep doing their old job at the same level. You're not adding a leader, you're just creating a bottleneck with a fancier title. When I built ShipDaddy and eventually Fulfill.com, I made it a rule: promotion means your old responsibilities get redistributed first, new responsibilities second.
Mike FullamCEO · Togo
The first thing I watch for is who solves problems before I even know there is one.
That person is not waiting to be told what to do. They are already thinking one step ahead of the operation.
At Togo, I promoted someone early on who kept flagging small gaps in how we were handing off shipments between modes. She was not asked to do that. She just did it because it bothered her.
That told me everything. She cared about the outcome, not just her job description.
The shift in responsibilities did not slow us down because she was already carrying more than her title suggested. The promotion was just catching up to reality.
One signal I always look for is how someone handles a bad day. Anyone can perform when things are smooth. Show me how you act when a load is late and a customer is hot. That is where real leaders show up.
If they stay calm, communicate fast, and own the fix, they are ready.
Bottom line: Promote the person who is already leading before the title. The signal is how they handle pressure, not how they perform when everything goes right.
Scott BrownFounder · Focus Group Placement
When I was expanding my product teams at Union Street Enterprises to other platforms like LevelSurveys and FocusGroupPlacement, I hired people who organically became the problem solvers even if they were not tasked to lead. The biggest indicator of future success was when someone made a habit of updating stakeholders on the status of their work without being asked to do so — showing they were thinking beyond just their own tasks and job roles. I'd gradually transition responsibilities with them providing leadership on smaller cross-functional initiatives at first, which enabled me retain the oversight while they demonstrated their ability to co-ordinate deliverables without creating bottlenecks.
Going through the restructure at WMD Alltagshelden, I learned to spot people who lift the whole team. One person shared a new way to schedule caregivers that cut our response time without adding work. That was huge. If you see someone quietly boosting everyone else's performance instead of focusing only on their own stats, they are usually the right choice for a promotion.
If you have any questions, feel free to reach out to my personal email
At Roy Digital, things move fast. I promote people who communicate clearly and adapt on the fly. One person stood out by volunteering to demo new AI tools, which helped us ship features much faster. I handed out more responsibilities in steps so we stayed on schedule. You know someone is ready when they get the whole team excited about a new challenge.
If you have any questions, feel free to reach out to my personal email
Nicolas MorvanGeneral Manager · Mava
This is one of the trickier balancing acts I have to play in my role at Mava, but when I pick out someone for their first lead role, I try to be seniority agnostic and look more towards how they deal with ambiguity. Higher levels of responsibility always mean more ambiguity, so if the person I promoted was already making decisions without needing constant direction and communicating those decisions clearly to others then they have already showed that they have what is needed at that level. That is always the strongest signal it would work. Before formalizing the role, I gave them ownership of a specific area so I could see how they managed that responsibility as a sort of trial run. It made the eventual transition to the promoted role smoother, so its encouraged me to make promotions based on behavior that is already happening and is visible, rather than on potential.
Stephen DoranDirector · Quickline Logistics
Promoting your first team lead is one of the most pivotal decisions you'll make as a founder; get it right, and you unlock scale, get it wrong, and you create friction at the worst possible time.
For us, operating in a 24/7, 365-day environment where a delayed decision can mean a missed delivery window, the stakes are real. We couldn't afford to slow down while someone found their feet in a new role. So the signal I looked for wasn't tenure or even raw skill; it was ownership mentality. I watched for the person who treated problems as theirs to solve before anyone asked them to.
The one moment that confirmed it for me was when one of our drivers flagged a route inefficiency; not just flagged it, but came back the next day with a suggested fix. No prompt, no agenda. That's the mindset that translates into leadership. In a business built on agility and real-time responsiveness, you need leads who think that way instinctively.
The transition itself has to be deliberate. We kept delivery responsibilities intact during the handover period, introducing leadership duties gradually so there was no gap in performance. We leaned on our technology, AI-driven route planning, and job management systems, to absorb some of the operational load while the new lead found rhythm in the role.
If you're scaling a service business, don't promote the loudest voice. Promote the person already acting like a lead. The title should confirm what's already happening, not create it.
Emma SansomManaging Director · Flamingo Marketing Strategies
When I need a new lead, I look for curiosity over experience. I remember one marketer who adjusted strategies based on actual client questions instead of following the plan. It worked. We use that logic at Flamingo. It keeps the work steady even when people take on more. Find the person who listens more than they check boxes. You won't see the quality drop when they move up.
If you have any questions, feel free to reach out to my personal email
The promotion proved successful because within two quarters, the team's overall output actually increased by about 20 percent. The new lead's investment in others' growth meant three junior developers leveled up significantly, and the collective output exceeded what any single senior developer could have produced alone.
Execution speed is visible. Alignment speed is invisible — but far more scalable.
If someone is already informally leading through clarity, the formal title just amplifies what they're doing. That's when you know the promotion won't break momentum.
Your best individual contributor rarely makes your best leader. Find the person your team already follows.
