Five Questions To Ask About Your Company’s Leadership Development


Rashaad Bajwa is the CEO of Integris, a premium, IT-managed service provider serving small and mid-sized companies nationwide.

Most companies say that leadership training is critical to their future. But is the message getting through?

According to LinkedIn Learning’s 2023 Report, only 26% of workers said their organizations encouraged them to learn a new skill. In Gartner’s recent survey of HR professionals, 24% expressed doubts that their leadership training programs were hitting the mark for their company. All this when LinkedIn’s data suggests that employees who’ve gotten leadership training are 75% more likely to stay with their current company.

It’s enough to make C-suite leaders scratch their heads and ask, “What went wrong?”

As the CEO of Integris, a national IT MSP formed from the merger of several successful IT companies, we’ve grown fast and thrust many people into new leadership roles. Developing common standards and practices has been a daily challenge we’re tackling. We couldn’t do any of it without the help of our leadership development program.

Building it, however, took a lot of hard work and the willingness to answer a few hard questions. I’ll share them with you here so that you can ask yourself these questions as you’re building your leadership development program:

1. Are you giving our leaders in training a chance to build a network across the organization?

It’s tempting to develop your leadership classes by departments or areas. If you do, you’re denying your leaders a chance to spend time with other experts across all your company’s departments.

Build cross-functional cohorts and give them a challenge to fix. You’ll be surprised how their knowledge cross-pollinates, and future leaders can learn about how the other departments work. Later, when problems crop up, it’s simple to pick up the phone to dial their buddy to collaborate.

The value this builds for the organization is tremendous, and it plugs your aspiring leaders into the orgainzation in a way they wouldn’t be otherwise.

2. Does your culture value feedback?

Do employees have a sense of psychological safety at your organization—enough to feel like they can bring problems to management?

You’d be surprised how many organizations would answer no to that question. Leadership training can help your company set a standard for management behavior, helping create a consistency of soft skills in leaders that employees can come to expect.

Our company has regular “office hours” on Microsoft Teams where employees at any level can ask the executive team questions in real time. They don’t hold back, and it’s brought a lot of important issues to the fore while they’re still in the early stages.

When you train your management to approach problems with curiosity instead of defensiveness and blame, you’re well on your way to having the right leadership standard to teach. The other benefit? You’ll create a “fail fast” culture known for taking risks and fixing problems—the hallmark of a truly modern organization.

3. How will you track your progress?

Things that get measured get done, especially when you’re training for soft skills. Just putting people through the class is not enough.

Have you considered a 360-degree rating program that allows employees to rate coworkers’ performance anonymously? We do this regularly, allowing us to pick up the minor leadership issues before they become systemic problems.

We also give our leadership training cohorts challenges to address, and we measure the effectiveness of those programs by how well we can implement their solutions in the organization. Either way, it’s a win-win.

4. How do your clients feel about your progress?

Do your clients feel you’re leading the company in the right direction? What systemic issues do they see? What opportunities should you seize?

In order to answer these questions, we’ve developed a client council that addresses these issues and has taken their constructive criticism right to our cross-functional teams to manage them. When action is being taken, everyone’s happy, and leaders-in-training get experience spearheading essential initiatives for the company.

5. Are you offering enough opportunities for upward mobility?

Annual reviews are lovely, but they should be about more than just feedback loops on an employee’s current role. This is the perfect opportunity to ask about an employee’s goals, offer them leadership training opportunities and help prepare them for the next upward step in the company.

If this question isn’t part of your review protocols already, it should be. Lack of advancement opportunities is one of the biggest reasons the best talent leaves. Don’t give them a reason.

There are always opportunities for leadership growth.

In an era where it can feel like the economy is treading water, it can seem like there are no new senior positions to offer. But I urge you to think creatively about your employees and their skill sets and look for opportunities to move them laterally and give them a new challenge or goal.

Paying for certifications, degrees and more can strengthen your leadership in ways you’ve never even considered and build loyalty. After two years, our leadership academy has already provided tremendous value to our company and improved our retention rates. What has your leadership program done for you?

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