The step that gets skipped is leadership development before headcount growth. Companies hire sellers and assume leaders will emerge on their own. Some do. Most don’t, not without a structure built to produce them.
Dean Elali, founder of OSP, has spent years building sales organizations that work with Fortune 100 companies including AT&T, NRG, Xfinity, Vivint Home Security, and Verizon. His view on this is direct: teams that scale without developing leaders alongside headcount are building something that cannot hold its own weight.
Why the Skip Happens
Growth creates pressure to fill seats. A manager who needs ten more reps this month will hire ten reps this month. Training new leaders takes longer and shows results later, so it loses out to the faster task.
There’s also a false assumption behind the skip: that a top performer will naturally become a good manager. Selling well and developing other people are different skills. A rep who hits every number alone can still fail to teach anyone else how to do it.
When a company promotes on sales numbers alone, it often ends up with a manager who cannot coach, a team that stops improving, and turnover that eats whatever the hire saved.
What Happens When It’s Skipped
The costs show up in a specific order.
New hires plateau early. Without a manager who can coach, reps learn the job through trial and error. Some get there. Many quit before they do.
Turnover becomes constant. Direct sales already has natural turnover. Skipping leadership development adds to it, because reps who don’t see a path up tend to leave for one that offers it.
The business stops being able to grow. A team led by one strong individual can expand only as far as that person can personally manage. A team with several developed leaders can open new territories, take on new partners, and grow without the founder touching every deal.
Dean Elali has pointed to this last point as the real difference between a company that grows and one that just hires. OSP’s model treats leadership development as the thing that lets the business expand into new markets and new corporate partnerships, not as an extra step once the core team is set.
What Good Leadership Development Actually Looks Like
It is not a one-time workshop. A few things separate real development from the appearance of it.
Structured Paths, Not Open-Ended Promises
People need to see what the next role actually requires, not just that growth is “possible.” A path with clear steps, like running a small team before running a large one, gives new leaders a chance to build the skill before they’re handed the responsibility.
Shadowing Before Authority
New leaders should sit next to an experienced one before they get their own team. Watching how a real manager handles a missed quota, a difficult client, or a rep who wants to quit teaches things a training manual cannot.
Feedback That Happens Often, Not Just at Reviews
Teams that develop leaders well tend to have short, frequent check-ins instead of long quarterly reviews. Small corrections early prevent big problems later.
Exposure to the Whole Business, Not Just the Sales Floor
Reps who only ever see their own territory struggle to lead once they’re responsible for more. OSP’s approach includes exposure to both the field and the operational side of the business, since the people picked for roles beyond selling need to understand both.
A Practical Starting Point
Companies that have already skipped this step are not stuck. The fix is not complicated, but it does take discipline.
Start by identifying the two or three people already doing informal leadership, the reps others go to with questions. Give them a defined role instead of letting the responsibility stay unofficial. Pair every new hire with someone a step ahead of them, not just a manager several levels up. And measure managers on what their team produces over time, not only on their own sales numbers.
None of this replaces hiring. It changes what hiring is building toward. A company that develops leaders alongside growth ends up with a structure that can expand. One that doesn’t ends up rebuilding the same team every year.
