CHAPTER 3

Getting Your Boss Onboard

Now you’re really getting somewhere with your onboarding campaign. You’ve made an effective inventory of your boardability assets (which also gives you a good checklist of items you still need). You’ve drafted a strong, one-page board résumé, one that coordinates well with your full-career résumé. You have some solid references ready to back you up. So are you ready to go live with your board-wannabe campaign?

Not quite yet. There is a next step for your onboarding campaign that may be the most crucial of all. Before you pick up the phone, send a text message, or slip anyone your business card, there’s one important player who may prove to be your toughest onboarding checkpoint.

Yes boss.

Assuming that you’re a board hunter who’s rising up the corporate food chain, your own supervisor is the go/no-go decision maker on your plans. If he or she is not supportive of your joining a board, it won’t happen.

There may be any number of Why-Not motivators at work. Some companies have longstanding policies against letting their talent serve on outside boards (General Electric under Jack Welch was noted for this).

There may be less formal, but just as effective, unspoken taboos on the idea within your corporate structure. There are still many bosses who see no reason for letting their top talent be displayed in outside boardrooms, where it’s assumed (not unreasonably) they’ll be ripe for plucking.

The current realities of business also dog your internal boardroom path. As I noted earlier, the golden days of top execs serving on half-a-dozen boards have gone the way of three-martini lunches. Now, one or at most two outside-board seats is the modern max for an employed executive. This is driven less by good governance concerns than the hard fact that day jobs devour far more time and bandwidth today, leaving less for sitting in someone else’s boardroom. For the executive pitching his or her first board role to the boss, even that single outside engagement could seem like one too many distractions.

There are some risky tactics available for navigating the Negative Boss Syndrome. I know of one case when an executive VP held an outside-board seat for several years—without ever telling her supervisor. She was a masterful organizer and managed to juggle vacation and leave time for board meetings without leaving a trace. But this sort of boardroom deep cover is more than most of us care to take on, especially given the potential career damage.

This makes having “the talk” with your direct report on your board goals so crucial. It sounds scary, and no doubt it can be. Yet, most of the time, the board-wannabe will receive a positive response. Furthermore, the discussion can be vital for tactical reasons as well. Most often, when execs in the corporate structure start getting ideas about joining a board, they’ll have a supervisor who’s already hit that career milestone. He or she may already sit on an outside board, have previous board experience, or network extensively with those who are directors.

You should see where this is going by now. Not only are bosses your boardroom gatekeepers, they can prove to be your most powerful board mentors. Seek more than just your boss’s permission—aim for buy-in and advice. What tips can they give you on making your board-search a reality? Who in their network of contacts are players in the boardroom world and is the boss willing to make introductions? (This approach actually helps your overall career—what boss doesn’t take well to being buttered up for his or her wisdom?)

Finally, drafting your direct report onto your board-search team can be a great source for board “leftovers.” Assume your boss has already made the move into outside-board roles. An eternal rule for board wannabes is that gaining that first board seat is a long, tough slog. But then, once your ticket is punched as one of the club, further board opportunities quickly start coming your way. Thus, in short order you go from not being able to get through the boardroom door to having more offers than you can handle. If your boss is facing this handy dilemma, a talk about your own board ambitions gives him or her a handy name to drop as a good alternate prospect.

Another advantage of early discussion is that it helps clarify the boundaries on your possible board commitments. Your organization and boss may well support your outside-board interest—in the abstract. But once you have a solid board query with specifics, you may face backpedaling. It’s wise to start with early discussion on parameters, what is acceptable, and what may not be. How much time away should be expected, and are certain times of the year off-limits? What committees would you be joining, and how will they add to your time commitment? Does this board have its meeting schedule for the next year set?

While having “the talk” is crucial to your board campaign, it’s obviously a moment of tension. Negotiation, deflection, and misunderstandings are possible. Here are several examples of how execs have approached issues at this stage and how to turn potential roadblocks into assets:

Q: “I’m an executive vice president with an industrial equipment manufacturer. My direct report is the CEO, and he’s been supportive of my goal of joining the boards of outside companies, even encouraging me and offering tips. However, a couple of opportunities have come my way recently, and in both cases the CEO subtly discouraged me from pursuing them. In one instance he suggested there could be a potential conflict, even though I consulted our company counsel and she saw no conflict concern. Another new offer has come up to join the board of a venture-backed company, but my CEO now says that it would take up too much time. How do I deal with these mixed signals?”

A: The conflict here may really exist in your boss’s mind—as in a conflict between the idea of his EVP building outside governance savvy versus the reality of what it means in practice. In consulting with “board wannabes,” I’ve found several who share your quandary. Today’s enlightened bosses realize that rising executives gain strong strategic and management skills in the boardroom, skills important in succession and talent development.

But the reality can clash with this goal. Serving on an outside board will certainly absorb at least some time and attention that you could be giving to your career. Bosses may not appreciate just how much is involved until they notice one of their reports skipping out for a board or committee meeting. In a way, you’re lucky your CEO is raising his concerns now, rather than after you’ve joined a board and have to juggle schedules. And, of course, some bosses don’t like their top reports out on public display in foreign boardrooms, where juicy networking opportunities could tempt them away.

But let’s give your CEO the benefit of a doubt and assume that he’s just overcautious about time and conflict issues. First step is an air-clearing discussion between you two to assure that he still supports your board ambitions in general. Then nail him down. Just what does and doesn’t he support? How many hours per month can you be spared for a board seat? What specific companies or industries would represent a conflict? What would he see as an ideal board opportunity at this point in your career? For the latter, is he willing to make a few phone calls to help you attain it? This would give him buy-in on the opportunity.

Next, go to work on your own to prospect some new board opportunities. Make sure they fit into the parameters discussed. As part of your fact-finding, get solid numbers on the meeting schedules and time expectations of a board slot, along with a good take on how serving on this company’s board makes you a better VP. Finally, go back to the CEO with your sales pitch and tell him you’ve found a great board opportunity that meets all his specs. Then, wait for him to blink first.

Sometimes, though, your supervisor’s pushback can be more passive. This makes direct confrontation less likely, but it also means you’ll need to dig harder to find the real sticking points.

Q: This is my second year as a senior vice president at the U.S. subsidiary of a large European firm. I’ve been with the company for eight years, and have a good relationship with my boss, the U.S. chief executive.

I’ve had some interest in pursuing a first outside board of directors’ role and mentioned the possibility to the CEO. However, he gently pushes the idea off into the future until “we get this project out of the way,” and it always seems that there’s a next project to take its place. I feel like a kid asking a parent’s permission on something, but being told “maybe” until I hopefully just forget the idea. How can I get to a yes?

A: Start by drawing the chief out a bit on your time usage and commitments (evaluation talks are a good time for this). How does he view your current productivity and effectiveness? Just how well does he view your performance on those “projects”?

If these grades are lower than you’d like, yes, you’ll need to work on your day job first. If you’re pulling all As though, and are a real asset to the company (and to the CEO), you have both a better case and leverage to pursue it.

“If you’re of value, the company has an interest in retaining you and in seeing you develop as a professional,” notes Dave Opton, founder of the Execunet business and career networking firm. If you’re proving yourself as a real hi-pot, your boss has a vested interest in keeping you happy. Opton observes that the CEO should be thinking, “If I get in this guy’s way, he’ll probably develop his potential as a senior leader elsewhere.”

Conflicts? Any corporation such as yours should have legal and compliance staff able to give a quick vetting of any board opportunity for potential conflicts of interest. “Often, there are fewer conflicts at your level than for a CEO,” observes Kathy Simmons, executive director at BlueSteps, the career services division of the American Society of Association Executives. More to the point, shouldn’t your boss assume someone who’s a senior VP can make such a judgment call?

Marshal your facts in advance, pin down your CEO’s concerns, and realize that you’re a valuable commodity going into the board discussion. You should be able to change some minds.

Of course, you may discover that the real roadblock to pursing an outside-board role comes not from within your company, but from yourself.

Q: I’m at a point in my career when seeking an outside-board seat seems realistic, but I haven’t raised the matter with our CEO at all. While I’m interested, and have seen some personal board possibilities, the topic just never comes up in my company. I’m not sure if it’s a matter of no one considering the idea of outside boards here, or if it’s just too taboo to discuss. Thoughts?

A: Launching your first personal board effort can indeed seem scary within some company cultures. “Some execs at large Fortune 100 companies live in fear of their CEO or board finding out they’re seeking an outside-board role,” notes Phyllis Shabad, a top career counselor who operates Executive Brand Coach. This fear reaches far beyond the top corporations, though. At an intense moment in your career, while you’re navigating inside strategic and political currents, the idea of announcing that you want to explore an outside-board involvement can seem risky indeed.

Yet like many life concerns, you should start by asking yourself whether your fears are coming more from your company or from your own mind. Remember the old saw that successful salesmen use—the first sale you have to make is to yourself. Review the reasons why you would make a valuable addition to a board and also how it would be in the long-term interest of the company to have a more valuable, seasoned exec with boardroom savvy on staff.

Lay out arguments on how this exposure benefits your current career track within the company as well as counters to potential concerns. Pitch this idea fully to yourself, screw your courage to the sticking place, and then raise the topic with your boss.

What will happen then? Shabad, who has worked extensively with C-level executives on career strategy, finds that “board fear” is almost always a bogeyman that exists in the execs’ mind. When she counsels them to raise the onboarding idea, they find “there wasn’t much pushback—the CEO ends up giving his blessing, and my clients thank me enormously.” As noted, if you’re at a career achievement point where you’re drawing board attention, you’ve already proven yourself a valuable leader in your field—and that’s someone the company wants to keep happy.

In making your pitch, it’s always good to have some intelligence from the other side—what are the concerns of CEOs and board members when it comes to their execs joining an outside board? At Boardroom INSIDER, we’ve answered a few questions that offer a peek into the boardroom subconscious on this.

Q: I’m an outside director on the board of a mid-cap company, and also chair the audit committee. Our CFO has been on the job for a couple of years, and we’re pleased with her work. The CEO told us that she’s been approached to join her first outside board of directors. On the surface, it doesn’t seem like there’s a problem here—the time and effort involved should be reasonable, and this company seems to be solid. But I have a few reservations about the backgrounds of some of their investors, and the litigation history of the industry overall. There’s nothing that raises any actual red flags—I should note I just have a gut feeling that our finance head could be joining the board of a company with an uncertain pedigree. Should I raise this issue to the board, or am I overreacting?

A: It’s important for mid-caps to set a sound policy on their top execs joining outside boards, but in truth few have done so, and thus set themselves up for case-by-case judgments such as yours. Still, the board’s role to “advise and consent” on the offer should be based on facts.

If you’re the only director with concerns about the company your CFO plans to keep, a first step might be a personal chat between you and the chief executive. Seek his views on this (without sending any negative messages at this point). Then talk with the CFO to judge her pitch on the board’s company and its people. Assure that she’s investigated the company’s filings, its leadership, its strategy, and litigation/legal history.

The CFO should have already weighed these issues and have good counterarguments to any concerns (after all, she’s the one who’ll be on the boardroom frontline if disaster strikes). If not, it’s reasonable to expect some more homework. As audit committee chair, you may be overfretting some of the dangers your CFO will encounter. True, the company involved may face litigation dangers—but there are few today that don’t.

Assume the best on the part of your executive team on this call. Trust your CFO’s judgment on this (and if you didn’t already trust the CFO’s judgment, would she hold that position?) Don’t stir up the rest of the board unless the CFO truly seems to be leaping before looking and gotten too few answers.

As I noted, the ideal strategy is to make your supervisor into more than someone who just accepts your onboarding campaign. She or he can be your most powerful booster in crafting a boardroom apprenticeship. However, this demands some research.

Start by expanding your knowledge of your boss’s networks. Take a deeper dive on her or him (it’s amazing how little most of us know about our bosses). What boards does the boss currently serve with, or has in the past? Who does she or he know in the boardroom world? Is she or he active in venture capital, private equity, or economic development circles? Work to make the boss’s network your network.

Board-Seeker Action Items

  • At your current company, what is the climate for executives serving on outside boards? Is there a written or unwritten policy on this?
  • Have you discussed the possibility of serving on an outside board with your direct report? If so, summarize the response, especially any objections.
  • If you have not had this discussion, list five reasons why gaining a board seat would be beneficial to the company and to you. Also, make a list of the five most likely objections you believe your supervisor might offer. How would you counter these?
  • Research your supervisor and other top managers to learn who currently serves on a board, or who has done so. Would the person be willing to offer mentoring advice?
  • List companies/sectors that could present conflict of interest issues with your current role.
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