Upgrade and upfill
Upgrading upon loyal employees is one of the hardest parts of scaling a business. It is also one of the most critical. The popular adage, ‘what got you here won’t get you there’ not only applies to
execution tactics but it can also apply to people. Since different stages require different skillsets and experience, full lifecycle leaders are exceedingly rare. As you scale, the absolute best
person to be ‘Head of X’ is often someone other than the current person in the role. This is one of the more challenging aspects of being an early stage CEO: you need to honestly assess the
capabilities gaps in each area of the business on a regular basis, then act compassionately but decisively when upgrades are required.
The same applies to the CEO role. The requirements of the CEO job will evolve from Doer to Manager/Doer to Manager to Manager of Managers. The skills required at each level are different. A CEO hiring
her own replacement at the right time can be one of the smartest moves they make.
All of this becomes even more difficult when title inflation occurs too early. Offering a C-level or VP title can be a powerful recruiting tool early on but this often creates challenges later as you
need to add senior, experienced leadership above current team members.
How to identify the deficits:
Look ahead: keep a close eye on the skills needed for your next stage of growth. For example, if your Head of Sales is great at jumping into deals with AEs and getting them closed, see
how effective she is at hiring A-level talent and scaling sellers who take a deal full cycle without her involved. Co-selling with a small team of AEs may get you from $5 to $10M, but hiring
and standing up a larger self-sufficient team will be critical in getting from $10-20M.
Think gaps vs. titles: it’s easy to get bogged down in the org chart specifics when planning leadership hires. Who will report to who? What’s the title? Who will feel infringed upon?
These are not the first questions to answer and can actually lead you astray. Instead, start with a clean slate and focus on the experience, abilities, connections and knowledge the company
needs to meet its core objectives. Once you’ve defined these, then think about roles, accountabilities and org chart specifics.
Consider timeline to perform: in many cases, the current person has all of the raw abilities to rise to the challenge, but it will take time. Coaching up doesn’t happen over night and
sometimes the need to is too pressing to wait. Consider the urgency of the need.
Learn on advisors: experienced board members and external advisors can help you spot areas to level up before they become obvious. The more exposure your board has to your exec team
(e.g. via presentations to the board or special projects), the more they can help. If you need advice in a particular area where you board can’t help, identify other top performing companies
based in your city that have been through the growth cycle you are entering. Find out who is leading the functional area you need help in. Reach out and ask them what they would look for in a
Head of X going into your next stage of growth. They will likely be flattered you asked and willing to share their perspective.
Be honest: deep friendships and loyalty can be a mental trap. Ultimately, if a member of your team is not right for the upcoming phase of growth, failing to address it becomes a
disservice to the company and them.
Re-align titles if necessary: first, work internally to define roles and structure without titles (see competency gaps vs. titles). When everyone is clear on that, conversations about
titles get easier. if you hire above an individual, consider whether a title adjustment is required. You might be surprised; this can come as a relief to all involved. While there is sure to
be some initial consternation, growth-minded professionals will likely embrace a world class mentor coming in and leading the way.
How to act on it:
Here’s the good news: you don’t have to treat a role shift, title change or departure like a funeral. Celebrate the individual’s accomplishments to date and speak openly about next steps for the
person’s career. If the company has progressed during their tenure, then they have built a great set of experiences and a compelling professional story.
There are several options:
Upfill: bring in a seasoned, proven professional above your current leader to drive the next phase of growth and help mentor this individual
Re-allocate: find another area to apply the skills that have been built to date by your tenured manager
Replace: at Netflix, there used to be (still is?) a common phrase delivered to people being asked to move on: “go be from Netflix”. This encapsulates the spirit of this difficult
process beautifully. If they helped the company get to where it is today, then you are in a position to be a strong advocate and reference as they seek their next role.