The most expensive mistake in technology sales is one almost every organization makes on purpose: promoting the person who made the most revenue into management. It feels like meritocracy. It looks like recognition. And it quietly removes the highest performer from the work they were good at, then puts them in a role for which they have no experience and sometimes passion. Marta Penda, who works in sales leadership in hotel technology, argues that this single habit explains a large share of the dysfunction leaders complain about later. Her case is not that top sellers cannot lead. It is that nobody bothered to check whether they could before handing over the team.
The Promotion Problem Nobody Wants To Name
“They promote for the wrong reason,” Penda says. “Most organizations make their best individual seller a manager as a reward, not because they’ve shown any evidence of being able to develop other people.” The emphasis here is on evidence. Companies that would never approve a six-figure spend without data will move a person into a role that controls a team’s entire output on the strength of a quota number. There is no assessment of whether the candidate has ever grown another seller, no track record of developing people, and no test of whether they can diagnose a deal they are not personally running.
The consequences follow a predictable shape. “Selling and leading are different disciplines,” Penda notes. “You end up with a manager who’s frustrated they’re not in control of their number anymore, and a team that’s coached like everyone should sell exactly like the boss did.” Both halves of that sentence are costly. The frustrated manager drifts back toward the deals, taking over calls, closing on behalf of representatives (reps). The team, meanwhile, gets coached toward a single style that worked for one person in one market cycle. Sellers whose strengths run differently either underperform against a template that was never built for them or leave. The organization reads that as a hiring problem and goes looking for better reps.
Rigor First, Judgment Live
Sales leaders tend to frame process discipline and human instinct as competing priorities, something to be traded off according to taste. Penda rejects the framing outright. “We don’t treat it as a balance; we treat it as a sequence.” That distinction matters more than it sounds. A sequence has an order, and the order tells managers where to spend their attention.
Her diagnosis of each failure mode is precise. “Rigor without judgment gives you a rep who hits every stage of the process and still loses the deal because they missed what the buyer actually cared about. Judgment without rigor gives you someone everyone likes who can’t forecast their own pipeline.” The fix is to stop coaching the first category altogether. “The rigor is non-negotiable and it’s structural. Discipline, stage definitions, deal reviews; that’s the scaffolding. I don’t coach that in the moment; we build it into how the team operates so nobody’s relying on willpower or good intentions to stay accountable.” Anything that depends on a manager’s mood, memory or Friday afternoon energy is not a system. Build it into the operating rhythm and it stops consuming coaching time. That frees the manager for the part that cannot be systematized. “The judgment gets coached live, inside real deals,” Penda says, with managers “sitting in deal strategy, asking ‘What does this specific buyer need to hear right now?’ not ‘What’s the next step in the playbook?'” The playbook question has an answer anyone can look up. The buyer question does not, which is exactly why it deserves a manager’s hours. The manager of my teams have developed an immense ability to think about the client’s needs and brainstorm with the reps on how to make it happen, they thrive in deal and terms negotiation.
What AI Moves, And What It Cannot
The arrival of AI coaching tools has produced two unhelpful reflexes in sales organizations: treat them as a replacement for management attention, or treat them as a threat to the craft. Penda’s position is narrower and more useful. “Let AI do the homework. Call prep, account research, spotting patterns across hundreds of deals a manager could never review manually; that’s exactly what these tools are good at.” The payoff is measured in reallocated time. “It gives reps more time in front of the customer instead of buried in admin, and it gives managers visibility they didn’t have before.” Note what is not on that list. The tools take over preparation and pattern recognition. They do not take over the moment in a room where someone has to read a person.
That shift changes the role of a sales leader, and Penda uses an analogy that repays attention. “A coach still tells you how to hit the ball. An orchestra director doesn’t play every instrument; they don’t need to. Their job is to know exactly what each section is capable of, bring in the right voice at the right moment, and shape all of it into something coherent that the audience can feel. That’s the shift coming to sales leadership.” The leader who built their identity on being the best individual instructor in the room is about to find that job automated at the margins. “AI is taking over the parts of the job that used to require a leader standing over someone’s shoulder,” Penda says. “So the leader’s value moves up a level. It’s no longer ‘Am I giving good individual instruction?’ but ‘Am I orchestrating the right people, tools, and moments so the whole thing plays in tune?'” This loops back to the promotion problem. An organization that selects leaders on personal closing ability is selecting for the skill machines are absorbing, and ignoring the one they are not.
Follow Marta Penda on LinkedIn for more insights on sales leadership, coaching, and building high-performing commercial teams.
