One of the hardest thing for any Type-A business owner to do successfully is to delegate. Some believe, “If you want it done right, you have to do it yourself!” They say, “Nobody can do it like I can do it.”  And this may be correct, but sooner or later you must delegate. There’s just too much to do in a growing business, you simply can’t do it all yourself.

It’s certainly a compromise, but we believe successful delegation is a two-way street. The owner must accept less than “perfect” performance. The employee or contracted services individual must move out of their comfort zone, develop new habits, and accept new responsibilities.

Here’s what we have learned after years of experience, most of which was painful. Perhaps it will help you delegate more successfully.

  1. Look for Extrapolation Learners. People who can extrapolate the underlying principle from an example and apply that principle to a new example they haven’t seen before are good candidates for delegation. Many people don’t bother looking for principles since they can get cut-and-paste examples for pretty much everything they need on line.

You will find many who say, “Like what?” to everything you ask, even when they have seen an example of the same principle in operation before. Avoid delegating to these people. Delegate only to people who glean overarching principles from the examples given in trainings and their own experience.

  1. Seek Integrity. When people do what they say, don’t drop assignments you haven’t regularly asked about, and voluntarily keep you posted on the status of their projects, they are good candidates for delegation. Look for people who take responsibility to get the job done and don’t blame others.

Avoid delegating to people who say, “They never got back to me” when you have to ask, “What happened on that project?” because they didn’t voluntarily inform you. Don’t delegate to people who have demonstrated they will only accept the minimum level of responsibility required of them in order to get paid.

  1. Look for Coachability. When people can take and apply constructive criticism, look for policies and procedures that can help them get their job done better and faster, and show steady improvement, they are excellent candidates for delegation.

Avoid candidates who take constructive professional critique personally or don’t seek experienced help because they so desperately want to appear self-sufficient and all-knowing.

  1. Seek Self-Starters. When people see the big picture and, without being asked, initiate appropriate action, mitigate a problem, or improve an unstable situation, they are great candidates for delegation. They still require some supervision, but are less likely to require micro-management.

Avoid delegating to people who have already demonstrated a need for constant supervision and vigilant oversight.

  1. Look for Mistake Learners. Accept that mistakes will be made. Look for candidates who learn from them, candidates that see them as an opportunity to get to the bottom of what happened, candidates who write new documents to prevent a reoccurrence, and candidates who can improve your company’s policies and processes.

Avoid those who hide or try to cover up their mistakes, or blame others (finger pointers). Seek to rid your company of those people who continue to make the same mistakes.

  1. Provide Incentives. Create a bonus structure for the folks you delegate to. Make sure you both agree on the metrics. Use your new bonus plan for just one year, so in subsequent years you can improve the requirements as you discover and fine tune what’s necessary to achieve the results you are looking for.


  1. Give Regular Reviews. Make the reviews more frequent in the beginning to avoid the formation of bad habits or misconceptions. Always come back to the principles. Always remind the candidate about the importance of sales, growth, and profitability. Go over the decisions they have made, validate the correct ones and offer advice on the ones that need improvement.

Delegation is an imperfect art, but you can mitigate the risk of failure by looking for the attributes in others that will give you confidence and peace of mind. You must train your candidates on the process knowledge and operating principles necessary to take on the responsibilities involved. Then you must give them clear goals and regular reviews – and let them do it their way.

We like to say, “When the cement is wet, you can move it with a trowel. When it gets hard, you’ll need a jackhammer.” So, overkill on orientation, make sure they know where the money comes from (sales!), and confirm that your candidate thoroughly understands the principles that will guide their decision making.  Then accept the inevitability that they will make mistakes, and they will make decisions that will be different that yours. Some of those decisions may even be better!

Who We Are

Michael Houlihan and Bonnie Harvey Barefoot Wine Founders

Michael Houlihan and Bonnie Harvey co-authored the New York Times bestselling business book, The Barefoot Spirit: How Hardship, Hustle, and Heart Built America’s #1 Wine Brand. The book has been selected as recommended reading in the CEO Library for CEO Forum, the C-Suite Book Club, and numerous university classes on business and entrepreneurship. It chronicles their humble beginnings from the laundry room of a rented Sonoma County farmhouse to the board room of E&J Gallo, who ultimately acquired their brand and engaged them as brand consultants. Barefoot is now the world’s largest wine brand.

Beginning with virtually no money and no wine industry experience, they employed innovative ideas to overcome obstacles, create new markets and forge strategic alliances. They pioneered Worthy Cause Marketing and performance-based compensation. They built an internationally bestselling brand and received their industry’s “Hot Brand” award for several consecutive years.

They offer their Guiding Principles for Success (GPS) to help entrepreneurs become successful. Their book, The Entrepreneurial Culture: 23 Ways To Engage and Empower Your People, helps corporations maximize the value of their human resources.

Currently they travel the world leading workshops, trainings, & keynoting at business schools, corporations, conferences. They are regular media guests and contributors to international publications and professional journals. They are C-Suite Network Advisors & Contributing Editors. Visit their popular brand building site at

To make inquiries for keynote speaking, trainings or consulting, please contact