Coaching Your Employees to Scale Your Business

We all know the basic things we need to level-up: sell more, train more, hire more. It’s easy to tell peers to build a mentoring program, send your supports to networking events, or job shadow to get the right people in the right seats. But on the ground level, what does that look like? At the end of the day, what are the tactics you need to follow to get everyone ready to scale?

We asked CEOs and HR leaders to give us advice on how to best coach your current employees to become leaders of tomorrow’s business. These are the actionable insights we got.

Give your employees a sense of ownership

Find ways to give your employees a sense of ownership over the company and the outcomes of their work. Some companies use profit sharing or make the company employee-owned to promote buy-in, but bonuses and money only work as motivation to a point. Once everyone is comfortable with their pay (which should probably be your first priority, but that’s for a different article), feeling ownership over the work they do every day will keep employees engaged.

So often managers and small business owners are scared to give up control of their projects, and then end up with way too many tasks to complete and employees that can’t grow. You’re going to have to delegate sooner or later. “Give your employees ownership as early as possible,” says Matt Lally, Founder of TheGiftYak. “Give them the responsibility of part of the business. Have them drive initiatives. Allow success or failure to fall onto them. Avoid micromanaging so that they can thrive or you can help them develop in their weak areas. Ownership is the most important part of developing a key employee.” Using a performance management software with goal-setting tools like Namely can help you track your progress toward company initiatives.

Once you assign initiatives and projects to your employees, you have to teach them how to problem-solve, says Whitney Hill, Head of Business Operations and Development at SnapADU. “Coach them to problem solve with the mindset of making the decision without you. If they were in charge, what would be the path forward? So often we stunt employees by not giving them enough opportunity to put forth discretionary effort and see those actions directly make the company better.” This sort of follow-up gives growing employees both the freedom to experiment without feeling like they’re jumping without a chute. Using a project management tool like Wrike can help you track projects and give feedback on upcoming tasks, even when you’re working remotely. 

Giving employees responsibilities that affect the bottom line of the company helps encourage an ownership mindset.

Make sure that the initiatives or projects you give your employees have a line of sight to the growth of the company—and make this explicit to them. Drewbie Wilson, Founder and CEO of LeadStages says, “Giving employees responsibilities that affect the bottom line of the company helps encourage an ownership mindset. When your employees show up to work each day with an ownership mentality as opposed to a salaried or hourly wage earner, they are going to go above and beyond in their service to the customer, creating value throughout the company, making them leaders.”

How does this particular project affect revenue growth, increase customer count, or reduce manual work hours? When you tie initiatives to countable metrics that drive the bottom line, you give employees a sense of ownership. 

Assign projects and provide feedback

Throwing an employee into a management position without any support is a recipe for failure: the employee may make their way in the short term, but will eventually resent the lack of support. Start by assigning ownership to projects incrementally and providing direct feedback on performance. 

Many business owners are so used to doing everything themselves, they assume that the way they do things is the best way–it’s what worked so far! But Sherry Morgan of Petsolino tells us that growing leaders isn’t about showing them your way, but letting them find their own way. “One of the things that I did upon coaching my employees is telling them what to do but not how to do it. I want to scale my business, so I want them to channel their capabilities that even I don’t know exist. I only know them based on their performance at work and their claims on their resume. Aside from that, I don’t know what else they’ve got up their sleeves. So, I let them show me.”

Evan Tarver of SellingSignals agrees, “Instead of giving them a strategy to execute, ask them to come up with the strategy themselves and share it with you in a one-on-one meeting. Instead of giving them a performance review, ask them to review their own performance and discuss during a meeting where you both compare notes. Rather than running a company meeting, ask them to run it. This way, they start to work the muscle of being a self-motivated problem-solver who can work with limited oversight to meet or exceed expectations.”

Sometimes you have to work closely with employees to grow them into leaders. This can be a major time investment on the front end, but the payoff is a self-sufficient employee who will act in the company’s best interests. “For my employees, a major hurdle is moving from well-defined tasks, where following instructions is sufficient, to more complex responsibilities that require them to think creatively and make decisions about the best approach,” says Katerina Manoff of ENGin. “When I first delegate these kinds of tasks to one of my team members, we tackle them together. I use prompts such as,

  • How would you solve this issue? 
  • How can we help this student?
  • Can you draft the outline for this presentation? 

Then, I provide feedback and ask targeted questions to help them improve their first attempts.” These guided fact-finding sessions are the first steps in a mentoring program that supports a growing employee. 

Use followup and feedback for mentorship

Pairing growing employees with a mentor sounds simple, and it is. But building a successful mentorship program takes followup and honest feedback. Engaging employees should be an ongoing process that builds on itself, but finding ways to gather feedback and provide support when it’s not working can be difficult.

Eden Cheng, Co-Founder of PeopleFinderFree helped institute a mentorship program at her company. “The crucial part is ensuring that our staff remains active and engaged throughout the mentoring process. We made sure that we conducted regular surveys in order to gain a better understanding of how the partnership experience was progressing. This feedback system still remains in place almost 6 months later, and it has provided us with valuable data that has allowed us to examine what is and isn’t working in our current program. We can then make the necessary changes to keep it relevant and effective.” A pulse survey tool like 15Five can automatically send your employees surveys every week to capture feedback and improve employee engagement. 

Incremental performance feedback and emotional intelligence are important in a mentorship relationship, says Matt Diggity, CEO and Founder of Diggity Marketing. “One of the things we did in the early days was asking them guiding questions and letting them come up with solutions. Directives never work, it is the emotional intelligence that comes into play. As a CEO, you must listen to their problems and at the same time show them that you trust them enough to solve the problems. Feedback is also necessary and when someone does a good job, praise them and let them know that you appreciate their contributions. This would boost their self-confidence and soon they would become leaders.”

Scale by shadowing at the right moments

Finally, do as your English teacher told you: show, don’t tell. Rolf Bax, Chief Human Resources Officer at suggests letting growing employees shadow you when you make the tough decisions. “If you want people to develop and hone leadership qualities, the best training you can give them is a front row seat to current leadership engaging in the daily tasks of leading a team of people. As our company grew, I made sure that high performers had access to our owners and myself as we made important strategic decisions. Scaling a business often involves considerable uncertainty and stress, both of which call upon superior leadership qualities, so giving employees access to leaders during these times allows them to observe how good leaders act under pressure.” 

Showing employees how you make decisions in the good and bad moments—and unpacking your thought process when it’s all over—gives critical context that results in real learning.

Tamara Scott
Tamara Scott
Tamara Scott is Managing Editor at TechnologyAdvice and, where she guides content strategy, writes vendor and buyer content, and maintains high editorial standards among content creators across several properties.

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