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What is the Purpose of Identifying Leadership Challenges in Strategic Planning?

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Leadership challenges are very real, even for the best of leaders. In fact, the best of leaders likely know what their challenges are which allows them to prepare for them and understand how to overcome those challenges. These challenges can range across several groups in the organization and do not revolve solely around the CEO or Executive Director, although frequently that’s who people think of when addressing this part of the strategic plan.

It’s important to remember that there are two pieces involved in identifying leadership challenges, real and perceived. Both are important and perceived challenges should not be dismissed, if the perception of an automobile company is that they are poorly made vehicles this is an obstacle the company will need to overcome. Often times perceived challenges are not as readily understood within an organization. This is another great opportunity to gather feedback from external constituents. Similarly, real challenges can be difficult to talk about like providing unrealistic goals without the resources to reach them (a common affliction in nonprofits).

In order to understand a breakdown of these challenges let’s look at them by grouping:

Board Challenges

Identifying the challenges of the board is critical. Often this critical analysis of challenges is something best provided by an outside source (consultant) in order to avoid your board feeling personally attacked by the very team that reports to them. Of course, this feeling is something no one wants to occur. There are common issues with boards (diversity, size, experience, meeting attendance, tenure, etc.), and sometimes there are uncommon issues (conflicting personalities, disagreement in direction, deferring to one voice, etc.). Each of these needs to be addressed here and ideally between this section and the planning section a clear path forward develops.

One of the more common issues for a Board of Directors right now is diversity, equity, and inclusion at the board level. While many organizations are working hard to correct this there is always an opportunity to do more.

CEO/Executive Director Challenges

The CEO/Executive Director is often the lightning rod of both good and bad feedback, receiving too much credit when things go well and too much blame when things do not. With that said, identifying the leadership challenges that exist for a CEO/Executive Director is critical and tends to fall into two groups. One item of particular note here is it is often difficult for a CEO/Executive Director to receive negative feedback about themselves and unlike almost every other group on this list this one is often directed towards an individual. It’s important for the CEO/Executive Director to remember this is about bettering the organization and putting its leader (themselves) in a position to succeed. With that said, there are two areas that typically get addressed here, a leader’s lack of experience in certain areas and areas within the organization that provide them challenges. Looking first at lack of experience, it is important to remember that no one is perfect and has everything, so if you’ve hired someone as your CEO with an operations background one solution to their lack of finance experience is hiring a more tenured financial leader. When looking at organizational challenges, this can be a resource issue, directional issue, or an external perception issue that needs to be addressed.

Senior Team Challenges

The senior team challenges often do not fall on an individual the same way the CEO/Executive Director challenges do. Instead, they tend to look at the sum of the parts of the leadership team. With that said, there are frequently a lot of solutions that come from leadership challenges out of this group. The example of the CEO not having significant financial experience fits well. Beyond being solutions-based, it is also important here to identify challenges within the organization that fall on the Senior team and addressing solutions that will fit for your organization, whether that be training, new hires, or sometimes replacement of team members. Whether it be an issue of personality, a lone wolf syndrome, or a lack of decision making, sometimes there needs to be an addition by subtraction and that is not always easy to hear. Replacement shouldn’t also be seen as an immediate response, for instance if there is a lack of experience in the Director of Development’s role, but your budget is $50,000 the experience is not the issue and finding a replacement at that cost with a lot of experience will likely not happen. Don’t use replacement as a solution if it is fixing a symptom and not the actual issue.

This section is often scary to everyone because it is identifying problems within the organization and people can feel attacked. Make sure you utilize this time to identify the true problems and unlike many other areas of the plan or within your organization do your best to dehumanize the response. See it as an opportunity to protect your organization, which is exactly what it is there for, as well as an opportunity for improvement.

Find our whole “Purpose of” series here:

You can also download our sample/template Strategic Plan Request for Proposal for free here, no sign up or anything necessary: Strategic Plan Request for Proposal Template

Needing to identify your leadership challenges, as well as the solutions that fix them? This is an area NMBL excels in. We have a history of fixing some of the most difficult problems and enjoy doing it at the same time. Reach out today to figure out how we can support your organization’s preparation for and fixing of challenges (hopefully before they arise).