In this episode we talk about promotions. You want to reward your best people by promoting them to new roles, but when and how? How can you avoid the dangers of bad promotions? We are here to help! In this episode we answer questions including: When should an individual contributor become a manager?How do you handle an employee that isn't growing with the business?What happens when two people vie for the same role?All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you! Your hosts: Sean Byrnes: General Partner, LucidFog www.lucidfog.comAsh Rust: Managing Partner, Sterling Road www.sterlingroad.comNic Meliones: Founder, Startup Coach https://meliones.substack.com/Reminder: this is not legal advice or investment advice. Q1: When should an individual contributor become a manager? "We have a great engineer who wants to become a manager. I don't think they'll be good at it or enjoy it, but we don't want to lose them. What can I do?" Promotions are bets on future performance, not rewards for past work. Wanting a great IC to keep producing is natural, but don't promote someone into a role you believe they'll fail at. Management is a different job, not a higher rung on the same ladder. Test the desire before you grant the title: Send them to a management training course. Five days of reports, emotion-management, and conflict-resolution role-play is a filter. It either kills the fantasy or proves they're serious. If they're serious, they'll learn the mechanics (1-on-1s, conflict resolution, the parts of the job nobody romanticizes) before they run a real team. Try a 50/50 split. Keep them contributing while they test-drive managing people. Low risk, high signal. Examine your own bias. Part of you wants the status quo: a great engineer shipping great work. But your job is also to serve their career. Ask what they actually want long-term. Often it isn't "manage people" – it's bigger scope, real decision-making authority, or more visibility. Answer that, and you frequently get more of what you want, too. Build a real IC path. Most people only chase management because they've been taught it's the only way forward. Show them ICs who've grown into the equivalent of VPs and the pressure to become a manager evaporates for the ones who never wanted it. Make being a senior IC as prestigious as being the boss. The trap: creatively forcing people into roles they don't fit. Architect real jobs that solve real company problems. Don't invent a "team lead" title for a team of one. Q2: How do you handle an employee that isn't growing with the business? "One of our earliest employees is great, but is quickly being left behind as the business grows. Their role is shrinking as the company grows. I'd hate to lose them — how can I help?" This happens at every fast-growing company. The job someone was hired for often doesn't exist six months later. Not everyone scales, and that's not a moral failing. Set expectations early and honestly, before it becomes a crisis. Tell the whole team, on a regular cadence: "The job you have today won't exist tomorrow. We'd love you to be first choice for the next one, but it's on you to show us." That conversation, held often, does more than any rescue attempt later. Invest, but keep a close eye on who is already pulling themselves forward. Coaching and training are worth trying. Importantly: people who scale are already training themselves, learning new skills, taking initiative. If you have to supply all the initiative to drag someone forward, it rarely works. You can only pull someone so far, and you shouldn't contort the whole org to meet one person where they are. Be honest that the odds are low. In most cases this ends with letting the person go. Give them a fair chance to find their place, but time is limited, and if they're not climbing this mountain, they're unlikely to climb the next one. The kindest move is often the exit. Help them find their next role. At a bigger company they may be iced out and miserable; as an early-stage specialist elsewhere, their zero-to-one strengths are a genuine asset. Watch where the pressure actually comes from. They may not feel it in the work, but they feel it interpersonally, early. The trigger is frequently the people underneath them: strong reports threatening to leave unless the blocker moves. That forces the hard conversation, and it's never comfortable to tell someone the team has outgrown them. Q3: What happens when two people vie for the same role? "I have two great salespeople who both want to become sales director. There's one opening, so I can promote one — but at the risk of losing the other. What should I do?" Don't assume your best AE becomes your best director. A great AE is a closer. A great sales director is a scaler: coaching, building process, designing the machine. Different job, different skill set. The percentage of great AEs who become great sales leaders is low. Hire (or promote) for the scaler. Retain both, explicitly. Tell each of them, independently, that you want to keep them. For whoever doesn't get the role, ask directly: "If it's not you this time, what do we need to do to keep you scaling with us?" Run a transparent process, and don't stall. Be open about how you're evaluating. Then decide. Moving slowly doesn't preserve the peace; it raises the odds you lose one of them. Don't let fear pick the winner. If you choose based on who might quit, you've handed the team control of the company. Promote the person you genuinely believe will do the job best. If the other leaves, that's unfortunate. You deal with it, the same way you do with engineers or anyone else. Create a second path so "director" isn't the only summit. Strategic account management, a senior IC track, uncapped commission – give a top closer a reason to keep closing instead of elbowing into a management seat they don't actually want. (Fast-growing teams often keep great salespeople selling by not capping commission.) Always be hiring. You may need to backfill at any moment. Plan for it before you're forced into it. And if you ever find an AE who's genuinely a great sales director, never let them go. --- The through-line: Every one of these problems eases when there's more than one way to grow. Give people a real IC path and management stops being the only way to ascend. Set honest expectations early and "you're not scaling" stops being an ambush. Build a second summit and one open role stops threatening two great people. Promotions go wrong when the org offers exactly one ladder and everyone's forced to climb it whether it fits or not.
