August 2026 Newsletter
Burning Questions from the C-Suite
From a Right Hand: Do I Need My Own Right Hand?
I get asked a lot if a Right Hand needs their own Right Hand. In many cases, the real question folks are asking is, Is it time to hire a senior leader reporting to the Right Hand? When should an organization level up the Right Hand’s directly reporting team and bring in someone with more experience, a more senior job title, and likely also a higher price tag?
Here are 3 indicators that the Right Hand might need to level up their team, plus one caution.
In the Developing stage, the Right Hand is usually a friend, family member, or contractor working part time. In the Selling stage, you build systems and a team, and often that’s when you hire your first full-time RH. During the Profiting stage, you create a well-oiled machine, and you begin to grow RH leaders across the organization, but most of them aren’t senior leaders. At the Maximizing stage, you are building to scale, and that’s when many companies invest in a two-deep bench with senior leaders working for senior leaders.
If you can predictably generate revenue, you can hire. If you can predictably generate profits, you can hire more expensive talent. Often we look at revenue and profit dollars to make hiring decisions when what we should be looking at is predictability of revenue and profit. It’s not about the bank balance, it’s about the level of control your operation gives you over the bank balance.
2. Is your bottleneck with leadership or efficiency?
If you have too many tasks to do in the time available, the first place to look is efficiency. Can you automate routine jobs? Can you speed up the workflow with better processes or technology? Can you get faster or better at assigning work to others? These things don’t require a second leader in the room.
You need a second senior leader when you need more human judgment than one person can provide. For example, if you want to increase the organization’s capacity to make decisions at satellite offices, or you need more bandwidth to make complicated judgment calls, that’s a senior leader. When you need to turn a strategy into an action plan and get everyone to follow it, that’s a senior leader. But when you just need more time in the day, that’s often more about efficiency than leadership.
Sometimes we reach for a hire because we feel overloaded, but we don’t stop to say, What are we actually overloaded with? What part of your world are you trying to offload? What is your actual bottleneck? Does it have to be solved by a hire or can it be addressed by technology, process changes, skills training, or workflow improvement?
3. Look at people-management responsibilities.
Most managers can supervise 7 direct reports before becoming too stretched. If you’re certain that you need the team size you have, but you struggle to give each of your people basic management attention, it might be time to bring in a team lead or supervisor to help.
When it comes to managing employees, there is no substitute for actual time and attention. If you’re managing below your own acceptable threshold, bringing in a second leader to organize, and support those relationships could make a big difference in performance and culture.
Caution: Right Hands, if you continually feel that your team can’t be trusted to get things done, the problem might be your own delegation skills. Focus on becoming the kind of leader who can get others to perform rather than spending energy finding, hiring, and training someone new.
Famous Right Hands: Smoke and Stack, Sinners
If you know me then you know that I don’t really do violence or horror movies. However, in honor of our newsletter editor August’s birthday last week, this month’s famous Right Hand pair comes from one of his favorite movies, Sinners. This record breaking movie follows twin gangsters Smoke and Stack as they attempt to open up a juke joint in their hometown and are confronted by a supernatural enemy. Smoke and Stack are identical twins, but they are definitely not interchangeable. Smoke is grounded and execution-oriented (literally!). Stack is charismatic, fast-talking, always wheeling and dealing. Michael B. Jordan, who plays both brothers, described them as having individual strengths and personalities that together make a whole. That’s a pretty good picture of a strong CEO/Right Hand relationship.
Often, the value of having another leader in the room is that they don’t bring exactly what you bring. One person sees the risk of a new deal while the other sees the opportunity. One works the room while the other works the plan. Smoke and Stack know where the other excels, and they divide the work accordingly. However, they stay connected. They don’t agree on many things but they consistently work towards the same goal. Despite their obvious strength as a pair, they are both very capable leaders in their own right: it’s actually very interesting to watch the actions they take when not with each other. Any similarities to your CEO/RH pair? Hopefully you have fewer vampires.
Links: Smoke and Stack Represent the Two Halves of Sinners’ Wound, Smoke & Stack's Names & Different Hats In Sinners Explained
Recommendation and Guest Article
When our clients need to make a RH hire, we send them without reservation to One Eighty Collective, where owners Andrea and Joanna and their team get it done. Frankly, these guys are outstanding. I have not seen a single misstep in 3 years of working closely with them. We asked One Eighty Collective to share their insider hiring tips with you. Below is the helpful article they wrote just for our readers. (If you call them, use Heather’s name to get favored nation pricing.)
Right Hand, Wrong Profile
By Andrea Rishmawi and Joanna Murphy
Right Hand hires come in many shapes and sizes: different industries, varying titles, and a multitude of reasons they're hard seats to fill. We work with CEOs at the exact moment they're making this decision, whether the hire is a VP of Sales, COO, or any other key player in a critical function. Here we'll share examples of two recent Right Hand searches that, on the surface, look nothing alike. Yet, as the stories unfold, you'll see the common threads that weave a similar pattern, and how both searches nearly failed in the same way.
News
The Audible version of the bestselling Winning Together: How CEOs and Right Hands Build a Relationship That Works is now available here! We know many of you have been waiting for this format. Whatever format you read, we’d be grateful if you’d leave a review.
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