Executive opportunities can be seductive.

If you’ve never held an executive position before—the opportunity, the power, the office, the salary—It can be heady stuff. Even at small organizations.

If you are an experienced executive, you know how difficult it can be to work in any other kind of role.

However, not all executive opportunities are created equal. Some are fantastic opportunities, with healthy organizations and great teams. Others are toxic, funky, sinking ships.

On top of this, every healthy leader has a high sense of self-efficacy. You believe you can make a difference. You believe you can influence and change things.

If you don’t believe that, you shouldn’t be in a leadership role. The downside? Sometimes leaders overestimate their abilities or underestimate the challenges. Sometimes they just aren’t given all of the information.

Most often, because they didn’t ask.

Yes, you are a candidate for the position. But that organization should also be a candidate for your skills, time and energy.

Interview them as well.

Here’s a secret that most boards, owners or outgoing CEO’s don’t want you to know: They aren’t really sure what they are looking for in an executive. Oftentimes it comes down to one of three things:

• A candidate who is not like a previous problem person. This is reactive and provides no direction or sense of why you are a fit.
• A candidate who is exactly like the person you’ll be replacing. This is change-resistant and uncreative. It indicates a backward-looking approach. While this happens in very conservative or traditional organizations. It is also common in organizations led by dynamic, entrepreneurial leaders. Generally, it is common with very strong & successful leaders to want to replicate themselves.
• They just like a candidate. Skills or capacity can be irrelevant. This is a subjective & emotional decision. It leaves you vulnerable to a change in opinions or the political wind.

12 Questions You Should Ask:

1. What are the critical priorities & goals of the board/owners? As an executive, you still work for someone and report to someone. Often a number of people. Make sure that you know and have agreement on what is most important to them.

This should include strategic or business priorities as well as organizational culture and values.

2. What are the major opportunities and challenges facing the organization? Look for their ability to answer this question and their awareness of the environment they are operating in. Ideally, they are a strong source of accurate and useful information.

Additionally, look for their ability to answer this question from both internal and external perspectives. In other words, they should be aware of the major operational opportunities or challenges as well as those coming from the environment.

There are no perfect organizations or situations. A great board or owner is looking for someone to partner with and will be appropriately transparent.

3. What has worked/not worked in the past relationship between the Board or Owner and the previous CEO? What would they like to change or keep?

Most of the time, you’ll only be offered this kind of information if you are being hired after a negative experience with someone. However, if you are following a well-liked and trusted CEO, they likely have developed an informal set of practices and habits in the relationship.

Unless you ask about them, they aren’t likely to think to tell you. You don’t want to run into a situation of getting hit sideways with uncommunicated expectations.

4. Are there any legal, health & safety or ethical issues or practices within the company, that you need to be aware of? Or that they want to change?

With this question, you are looking for a number of things:

First, it’s the face-value answers. You’ll want to know what you are walking into, especially since you may be held responsible for it.

Second, you are looking for patterns and time. Does this organization show a pattern of operating unethically? Have they tolerated unsafe work practices? For how long? Why?

Third, are they willing to be open and honest with you? Immediately walk away if they aren’t.

5. What is their financial position? What is their financial philosophy?

This is very similar to the previous question. You want to make sure you know and can handle whatever you are hired into. You also want to make sure that you can get the quality of information you need when you need it.

Additionally, you want to start to gain a sense of their risk tolerance, their views on growth, diversification, savings, caring for employees, shareholders, etc.

Even if the organization isn’t a business, it needs to be healthy financially. You’ll want to know what that looks like to those in charge.

6. What will be your scope of decision-making authority? This may be an evolving conversation, but you should always know where you are at in any given point of time.
   • What decisions are off the table?
   • What decisions require a consult with the board or owners?
   • Which decisions are fully yours to make?

7. What control will you have over personnel decision (Including others in management)?

This is very similar to the previous question. What is unique here is that it isn’t uncommon to hear, “You are free to make whatever choices seem right,” and then discover that there are a few protected people, roles or “rights” reserved by owners or board members to just drop in new hires or promotions of their choosing.

Best practices are that a CEO has a free hand with personnel decisions – to create the best possible team to accomplish the goals.

The reality is that often there are conditions or exceptions to this. If they exist, make sure you know them, are comfortable with them and can succeed in that context.

8. What does turnover look like here?

High turnover is nearly always an immediate warning signal. Management will nearly always blame it on compensation. But it nearly always is tied to job satisfaction or workplace relationships.

If unhealthy levels exist, you’d be wise to suspect that there may be a problem. Ensure that you have a free hand to correct it.

On the other hand, extremely low turnover can sometimes represent another problem. In many ways longevity and loyalty are assets. However, it’s worth exploring the following:

• Are low performers being retained?
• Are there “old-timer” cliques?
• Will they shift loyalty to a new CEO?
• Are they open to changes?

9. How does the leadership or management team relate to each other? Are you walking into silos, turfs, and conflict? Are you walking into camaraderie and mutual support? Are they (unhealthily) competitive with each other or collaborative? What are their expectations in terms of being led?

You’ll want to know this in advance and determine if it is an environment you can excel in.

10. How will your performance be measured?

You will be assessed. There is a high chance that the assessment will be more informal than formal. This isn’t best practice but it is how it works.

Make sure you know, and keep current, their expectations for your performance. Make sure they are specific, make sense to you and are achievable.

11. Will they provide you with support for personal/professional development?

As an executive, you need to continue to grow. You need to be exposed to new and other thinking.

You will also likely find that you’d benefit from someone outside your organization to bounce ideas off of or confide in.

This can look like training, executive groups or masterminds, mentors or coaching. A board or owner that doesn’t understand or value this kind of investment is severely limiting your ability to perform and improve.

12. Can you talk to employees now? Talk to those that you will lead, at various levels, roles and locations. If you can, “shop” the workplace – do so. Even when this isn’t possible, interview people. Visit the locations. Gain a sense of:
    • Do they seem happy at work?
    • Are they doing their jobs well?
    • Do they seem stressed?
    • What does the workplace environment look like – does it show signs of pride and care?
    • Is there a respectfulness towards each other and customers?

You may also see things with a “troubleshooting” eye. Noticing what could or should be changed. However, also look to see strengths and assets. What makes people proud, what motivates them, what gets them up in the morning?

Here is what will happen: An ideal board or owner will probably not expect these questions. They may not even be prepared with answers to all of them. But they will be glad that you asked them and will work with you to get answers. Their respect for you will increase. As will their confidence.

You are asking the right questions.

They will see you as a partner to accomplish the goals that they have. They will work to build a strong relationship with you.

A non-ideal board or owner will become defensive, minimize the importance of the information will hide or distort information. Let them self-select themselves out of the skills you have to offer. There are plenty of other, better opportunities. Don’t waste your skills and energy on the wrong organization.

Take good care,

Christian

P.S. Would you like to learn about the fastest and most direct path to increasing your leadership confidence and abilities? Contact me at christian@vantageconsulting.org or 907 522-7200.