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Leadership questions: Fixing ineffective leadership


They’re your most trusted business advisors. Your leadership team has likely been with you a long time, many of them probably from the start. But now that your business is growing, does it seem like some managers are in over their heads? Before you reach the conclusion that someone in your inner circle is no longer the right fit, consider the possibility that they may simply be complacent or uninspired, rather than incapable.

Here are leadership questions to help you tell the difference.

1. What’s the problem? What’s really missing?

It’s easy to misidentify complacency as a lack of ability. Before you tell a manager, “You no longer have what we need,” make sure you’ve covered all the bases in detecting the problem.

Do you have an understanding of where you want the organization to go, and have you communicated that vision to your managers? Ideally, this would have been established when the company first started. But if not, low-performing members of the leadership team may simply think they’re doing a great job because there’s nothing formal in place for gauging their progress.

For instance, if your CMO isn’t marketing the company at tradeshows as often as you’d like, maybe it’s because she doesn’t realize you’ve earmarked supplemental funds she can use without blowing her annual budget. Don’t assume leaders know something you haven’t communicated to them directly.

Or, maybe your COO thinks he’s doing his job well because sales are through the roof, despite the high turnover rate in his salesforce. If he’s only focused on growing revenue, he could be missing the bigger picture. It’s important that you ask him targeting leadership questions to help him understand how his shortsightedness negatively impacts the entire organization.

Communication is key. Without a clearly articulated mission, or goals and benchmarks for measuring and recognizing success, even the most capable managers may miss the mark or become lackadaisical. It’s hard to follow a path that doesn’t exist.

If you’ve adequately painted the vision for your leaders and can reasonably rule that out as the problem, maybe your connection with them has merely gone stale and they’re uninspired. It happens – with marriages, friendships and, yes, even professional relationships.

That doesn’t mean you have to like everyone on your leadership team, but you should all share a concrete understanding of what the organization needs and what it will take from each person to get there. It comes down to rigor and relevance – people are naturally more motivated when they know what’s expected of them and believe their contribution matters.  By asking the right leadership questions you will reduce any misconceptions.

2. Has the problem always existed?

Chances are, it hasn’t. You obviously had good reasons for choosing each member of your leadership team. What were those reasons? Revisit them. This can help you pinpoint when the problem first occurred and what may have caused it. Other leadership questions to consider are to ask yourself if  there are underlying issues, such as redundancies or holes in your organizational structure, which may be contributing to your managers’ shortcomings. Have you empowered them with the authority to make critical decisions and get things done?

For example, if your email server has always been reliable, but lately it’s down more than it’s up, that doesn’t necessarily mean your CIO is dropping the ball. Maybe your company’s bandwidth needs have recently outpaced the IT department’s hiring budget, and thus, its ability to employ contractors to help expand the infrastructure. Or, it could be time to consider new technology vendors better equipped to meet your company’s technology demands.

Finding the answer to these questions can help you determine if you have the right people in the right jobs to grow your organization. You’ll have a clearer understanding of whether the problem is the result of managerial inefficiencies or circumstances that have evolved over time.

3. What’s the best solution?

Once you’ve determined the true problem and what created it, you can make an informed decision about an appropriate solution. You may find that providing your managers with additional training or resources, or an opportunity to improve, is all that’s needed to right the ship. If so, sit them down and tell them that, although they’re excelling at A, B and C, you really need them to step up and commit to doing D, E and F as well. Give them time to make the changes and then decide if they’re the right fit or not.

By looking for ways to salvage the situation first, you help avoid making a hasty decision that could be detrimental to your company. Still, there may be times when you come to the harsh realization that your organization has legitimately outgrown some of its managers.

For example, your best friend from college has been your bookkeeper for years. When you handed over managing the company books to her, it was a relief. But, is she willing – or able – to be the CFO of your growing company? Sure, she’s worked endless hours to keep your organization on track and compliant. But what about strategy? What about your financial picture five years down the road?

If she doesn’t have the skills or credentials to take your company to the next level, it’s probably time to part ways. You should always follow proper, established procedures for terminating an employee – whether they’re on the leadership team or not.

Having the difficult conversations

Coming to the decision that it’s time to let someone on your leadership team go can be gut-wrenching. After all, you’ve probably been through a lot together, so there may be an emotional bond. Here are some suggestions for handling the difficult conversations and transition period that will ensue. Let’s assume the manager being terminated is named John.

  • Be respectful and honest with John. Explain to him that the company needs to do X, Y and Z to remain competitive over the next five to 10 years. Let him know you’ve come to the conclusion that his specialty and passions don’t lie in these areas, and that you feel it’s better for him and the company if he pursues something else where he’ll excel.
  • Be open and direct when discussing John’s departure from the company with employees. Explain to them the direction the company is going. Tell them you’re making this change for the future of the company. Let them know you’ve discussed with John the fact that he probably isn’t the best fit, and that he deserves a position that suits him and makes him happy.
  • Remember, telling employees about the departure of a key player doesn’t mean sharing details that should be kept confidential, but your employees deserve to know what’s going on and why.

Addressing these tough topics in a deliberate, professional manner allows John to keep his dignity while also helping you avoid falsehoods with your workforce. You demonstrate to everyone what it looks like to show respect in a difficult situation – and your employees will appreciate your humanity.

Escaping the messiness

By the time a gap in capability or experience appears in your organization, it’s probably already reached a critical stage. You’re in damage-control mode. The same usually holds true when ineffective leadership is caused by complacency or lack of motivation. But, it doesn’t have to be this way.

The elegant way to avoid this is to have regular conversations. Sit around a table with your leadership team three or four times a year. Ask yourselves:

  • What would it look like if any of us were no longer qualified, and how would we fix that?
  • What skills and abilities do we need to grow in order to be successful in the future?
  • Is there someone who could and should do this instead of one of us?

As a business leader, it’s your job to look for gaps in experience and management, and assess your team’s ability to lead in the future.

Implementing change

If you determine a management change is needed, get some advice before making a big move. Bring in a consultant who can help evaluate your team and make recommendations for the future. It’s a big investment. But, when compared with investing in a C-level salary that may not be what you need, it’s a drop in the bucket. Advice from someone in your industry who has been where you are can be invaluable and help you avoid impulsive decisions.

A final thought: When you’re hiring, make sure you’re hiring for your organization’s needs five years down the road – not the needs you have today. Planned leadership builds a solid foundation for your business and instills confidence in your employees.

Looking for more inspiration?

Running a company isn’t easy. For more helpful tips on how to make the most of your leadership team and workforce, check out our e-book, HR Outsourcing: A step-by-step guide to professional employer organizations (PEOs).