Don Quixote adn Sancho Panza

Who is your second in command; sidekick; foil; number two?

Your business has grown or you are ready for your next adventure, either way, you will need a loyal sidekick who does what you do, as well as you do it. In short, you need a good Number Two, General Manager, Chief Operating Officer, a second in command. Somebody to manage day-to-day operations, while you concentrate on planning and other senior management functions.  Military organizations are the leaders in identifying and training for the XO (Executive Officer) or 2IC (second in command). Finding yours, will take deliberate planning and active managing – but it will be so important to the future of your creation.  If you are growing your business to sell in the future, this person will be integral to helping the new owner develop a seamless transition for the customers, employees and your succession plan.

Just under half of all new managerial hires fail within the first 18 months. However, you can significantly change the odds in your favor if you take the time to do it right.

You Can’t Get Who You Want Until You Know What You Want.  The first step is to define what you’re looking for. This focuses your search and ensures that your new deputy can do what you need them to do. This description must include both the functions the job involves and the kind of person who would best perform these tasks. It may help to use an automated program like this one ( to streamline this process.

However you put it together, your job description should map three core areas:

  1. Experience
  2. Qualifications — (not just academic qualifications, but also knowledge of the industry and your competitors.)
  3. Character and personality — (includes characteristics {tenacity, attention to detail, etc.} necessary for the challenges your company faces.)

You may not find a perfect match for the position, so divide your list into what’s essential and what’s desirable. During the selection process, it’s easy to be swayed by a candidate who has all the desirable attributes but who lacks qualities essential to your needs.

When Looking For a Second in Command, Don’t Look For a Replica of Yourself.  Your company probably needs somebody who complements the skills and experience you have, rather than duplicating your strengths. Sometimes having a trusted business adviser review the job description will be helpful.

Set a Salary Range and Benefit Package.  Once you’ve completed the job description, you need to set a salary range and benefits package. Review job-search websites to see what similar positions offer. When you know what you want in a number two and what you can offer them, then it’s time for the search to begin.

Where to Look. 

  • Look among your existing employees first. They know your company better than any outsider. You also have had a chance to observe them, and can see first-hand their strengths and weaknesses. However, if you consider in-house candidates, you MUST be as rigorous in your assessment as with outside applicants.
  • Use all networking possibilities available. Your strategic business partners are an often-overlooked source of leads, so don’t forget to inform them. Above all, be systematic in spreading the word. Make sure to tap into professional organizations, as well as family and friends.
  • Employment websites and LinkedIn are powerful tools in your search. Your Web ad can be much more detailed than a typical newspaper ad, narrowing responses to those who are best suited. In addition, the “search and find” feature on job sites allows you to find key words on your “wish list” more efficiently than sorting through a stack of paper resumes.
  • Traditional print advertisements may be costly but are useful if your needs are particular to your industry. As with Internet ads, the more accurate and specific you can be, the better the quality of the responses.
  • Headhunters may be effective, but typically cost 25%-35% of annual salary. They’re worth considering in a tight market or when your needs are unusual or very specific.  Make part of the payment contingent on the new hire lasting a certain length of time.

Keep ‘Em or Throw ‘Em Back?  It’s a giant step to hire a number two, and the biggest issue is trust. You have to feel comfortable with your new sidekick.

  • The rule here is to trust your negative intuition and confirm your positive feelings. If everything seems right about a candidate, but your gut feeling is a contradictory and strong “no”, trust your gut. If you’re just delighted to welcome somebody on board, stop and take a few days to think it over. This delight is akin to “falling in love” – the feeling will often pass, so waiting is part of the process.
  • Have a neutral third party check them out.
  • Run a full background check including a credit report.
  • Confirm all references and educational records.
  • Always have a trial period, for both parties to evaluate the new working relationship before making a more definite commitment.

Welcome Mat.  Make sure that your new number two gets off to a good start. Have a place set up for them to work, and have everything they need there when they start (e.g. phone, supplies, computer, etc.). They should feel comfortable and welcome in your company.

Most important, make it clear to other employees that the newcomer is your careful choice. You expect them to do all they can to get their new colleague up to optimum performance. You need to grow your company to its full potential. That requires a team effort — from you, your number two and all your crew!