Asking for career help: How to ask the Chairman of the Board for his advice [script]. - Westgate Career Coaching

Asking for career help: How to ask the Chairman of the Board for his advice [script].

Do you struggle to ask senior-level business people for career help? Do you feel shy at the thought of asking someone you don’t know for advice? Here is a simple plan that you can customize for your own style that won’t leave you feeling exposed.

The value of mentorship can be exponential and asking the right people at the right time will open doors to opportunities. Asking for help in the appropriate way will connect you with influencers in your target market.

career help

Here’s how to do it. Write a letter that is clear about what you want. Create context and demonstrate that you have “street creds” in his wheelhouse with enough detail to pique his interest. In this case, marine intermodal transportation.

Dear Mr. Chairman:

As a 27-year CISO veteran in the logistics industry, I would be grateful for the opportunity to learn from you, with no strings attached. I’ve followed you for 18 months, read your position paper on cyberthreats, and watched all of your keynote speeches on

My promise to you—should you agree to this arrangement—is that I will only ask you for information, nothing else, no referrals, no job opportunities, and I will guarantee you I will not pursue opportunities at your firm or its board. I will keep our arrangement confidential.

I am particularly interested in your perspective on cybersecurity issues at the board level. What are the specific areas that boards need to focus on to mitigate risk? How do boards evaluate board readiness for outside directors?

The suggested structure of this arrangement could be a six-month engagement of one-hour meetings at a location convenient to you or by telephone or Skype. I realize this is a lot for me to ask and a lot for you to give to someone you don’t know. However, I am confident that your insight will help me execute on my strategy.

Of course, if there is anything I can do for you, I would be pleased to discuss. I also understand, Mr. Cruz, you may not be able to accommodate my request and so I will telephone you on x date to determine your level of interest.

[You must follow up when you say you will. This is absolutely critical to your process. Keep the letter short because if it is too long, it won’t be read].

In this scenario, the individual is targeting an external board of director opportunity, so you may want to target individuals who have served on public boards in your targeted area of expertise. These individuals will be able to help you create a plan so that you become attractive to a public board. They will help you understand the process of landing a board seat, for example, and help you navigate the landmines you will need to navigate once you land a board seat.

I believe you will be pleasantly surprised at the results of your campaign and will achieve your goal in lightning speed. I know this approach works because I’ve used it myself as have my clients. Simple, clear, and direct approaches are effective.

If you are still feeling uneasy about this approach, consider this question: “What do you have to lose?” The benefits far outweigh the risk.

For more information on mentorship and networking, see Harvey Mackay’s famous book Dig You’re Well Before You’re Thirsty—the only networking book you’ll ever need.

If you need a customized plan, contact me today. Launched in November of 2017, The Customized Job Search Coaching Program using the hidden job market to land a better job faster is one of the most popular packages in the history of the firm. This is a 6-module strategy plan that you can begin using immediately.

“However beautiful the strategy, you should occasionally look at the results”
– Sir Winston Churchill

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