Illustration: Oscar Ramos Orozco

Finding (And Keeping) The Right Advisors For Your Business

No matter how ambitious or talented, we all have our blindspots – certain obstacles or hard realities that we fail to anticipate. Which is why we all need some sound advice from time to time. To get it, we must engage the right Advisors along the way.
Perhaps because of their necessity, we’re prone to throwing around the term “Advisor” much too loosely. Many entrepreneurs assemble a board of Advisors and then have no idea what to do with them. Similarly, industry veterans agree to advise businesses without any clear sense of responsibility.
An “advisorship” is much more than a mentorship; it is a relationship between a business and a third party that has a specific value to add. There is an implied sense of expectations and reward. Just as an Advisor must invest his or her time to serve the business, the business must invest time into the relationship.But what comprises a really great Advisorship? Let’s take a look at how to engage, incentivize, and manage your Advisors.

How To Engage The Right Advisors

  • Select advisors based on areas of expertise. Every business needs a dream team, but you can’t hire for every expertise you’ll need. Sure, you may need developers and designers, but how about experts on your industry or people with relationships with certain prospects that you can’t afford to hire? As you identify areas of expertise that you lack, consider who might be able to help.
  • State expectations up front. It is best to have a contract that covers details regarding any form of equity grant or compensation as well as whether or not expenses are reimbursed. Some entrepreneurs explicitly state the frequency of meetings, phone calls, and possibly the number of hours expected from a committed advisor.
  • Keep a candid exchange. Your relationship with your advisors should be constantly optimized through candid feedback exchange. Entrepreneurs should ask their advisors the question: “How can I better utilize you to help the business?” Likewise, great advisors always ask the question, “How can I be more helpful to you?”
  • Have an exit strategy. Most entrepreneurs I know say that their “advisors” have less than a 50% success rate. Granted, great Advisorships are a two-way street. That being said, it is fair to expect that some of your advisors will flake out, change industries, retire, or simply be too busy to help. As such, it is best to define up front what happens if either party decides that it’s not working out.
Once you have engaged your Advisors, you will want to ensure a productive relationship. Advisors can become a burden – in both expense and time wasted – unless they are managed wisely. Obviously, a great Advisorship is a shared responsibility between the leader of the team and the Advisor. Teams must select Advisors for the right reasons, engage them properly, and then manage and utilize them – purposefully and consistently – over time.In the spirit of advice, I reached out to a handful of legendary Advisors and entrepreneurs with experience on the topic and asked them to chime in.

How Can I Make The Most of My Advisors?

Guy Kawasaki
Entrepreneur, Former Apple Chief Evangelist, & Author of “Enchantment

  • Ask. If you don’t ask, you don’t get. The reason you signed up advisors is because they are successful, connected, and knowledgeable people. This means they aren’t idle. If you want their help, you’ve got to ask for it. You will sit by the side of a river for a long time before a roast duck will fly into your mouth. 
  • Know. Basically, there are three kind of advisors: “Mom” for adult supervision, “Jerry McGuire” for connections, and “Barack” for high-visibility window dressing plus those with specific technical expertise. The trick is to ask, or more accurately “use” each advisor in the right way. For example, using “Mom” to introduce you to Pete Cashmore at Mashable isn’t going to work. Neither will asking “Barack” whether you should use RackSpace or Amazon Services. Figure out what advice you need and who can help you in these areas before you even recruit advisors.
  • Pay. If you’re going to ask, you should be willing to pay. Actually, you should be happy to pay. An entrepreneur recently offered me 10,000 options in a company with approximately 20,000,000 authorized shares. A large turkey walking on the ground is more likely to show up on the radar than an offer like that. 0.01% is where it gets interesting, 0.05% is where you’re talking turkey. An advisor’s magic number is $1 million upon liquidity. Assuming no dilution (which is not a good assumption), this means you need to sell for $200 million. If tenths of a percent of options for an advisor causes too much dilution, then you’ve failed anyway. You’ll either make more than you ever dreamed or the company will fail.

Jeffrey Bussgang
General Partner at Flybridge Capital Partners, Author of “Mastering the VC Game

  • Hard, honest advice. The best advisors give you the hard, honest advice – not just act as cheerleaders. Think Simon Colwell in American Idol, not Paula Abdul.  Sometimes, you need be told you suck.
  • Push AND pull.  Look for folks who are thinking about your company in the background at all times – sending you articles, making relevant introductions, asking probing questions whenever you send information out.  It’s great to have an advisor that “pulls” you into situations and dialog, not just folks who respond when you “push” for input.
  • Respect. Although many senior advisors may have more experience and perspective than the entrepreneur, if you don’t feel like they’re treating you with the proper respect and deference, don’t waste your time.  Some advisors get confused about their roles. They’re not chairman of the board or a majority shareholder. It’s your start-up. You can solicit input, but in the end, you make the final decisions and are accountable for the results.

What Makes A Great Advisor?

Fred Wilson
Managing Partner, Union Square Ventures


  • When you advise a founder/CEO, understand that they will only take a small fraction of it.
  • Advisory roles require face time. Regularly scheduled breakfasts are great.
  • Advice given privately is taken more often than advice given publicly.
Founder of VaynerMedia & Author of Crush It 

  • Under-promise and over-deliver. Early on, when I was an advisor, I thought I could impact the businesses I advised in too many ways. Now, I try to under-promise and find specific ways to add value.
  • Keep the companies top of mind – always. I use icons at the top of my computer for each of the key people/companies that I am advising. When I’m in meetings, I often take a glance and think about what I can do at that very moment.
  • Strike early. Do something great for the company you’re advising early on – whether it’s making the connection for a new hire or key introduction, or helping them close a deal.
The message is loud and clear: A great Advisorship, like any other relationship, requires energy, communication, and commitment. Pursue advice, but with a commitment to do what it takes to set up your advisors to succeed.
What’s Your Take?
What qualities make a great advisor in your experience?
More insights on: Collaboration, Hiring, Office Dynamics

Scott Belsky

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Scott Belsky is Adobe's Vice President of Community and Co-Founder & Head of Behance, the leading online platform for creatives to showcase and discover creative work. Scott has been called one of the "100 Most Creative People in Business" by Fast Company, and is the author of the bestselling book, Making Ideas Happen.
load comments (7)
  • Steve @GraphicDesignBoss

    Great post – In terms of a small business design agency my ‘advisors’ are a good accountant, good lawyer, and good suppliers.

    The one thing I don’t have which I think I need is a coach to help me improve how I land new new business and also look at my business from a strategic perspective.

    How about anyone else in small business?

  • chrisjohnf

    @Steve: I think it all really depends on what you as an owner wants to achieve. Keep the firm small? Take on volume jobs? Take on select jobs? How many projects a year are you willing to take on? What sort of scale do you want to engage in (5k project or a 100k project)? Self generating content (use your firm to create your own content or business ideas)?

  • Zara

    Very interesting–I wonder if any of you have a sense of how advising works in the non-profit world? I have a hard time imagining myself (creating an arts organization) being able to pay for advice…but I know I’ll need advice. Any suggestions?

  • Maren Kate

    Freaking awesome!! Best article I’ve read on this :)

  • Ian


    Great tips & I would add:

    First off – define your compelling story – everything and I mean everything flows from that.
    Then decide 3 things –

    1.What role will an adviser play in the context of your compelling story – 9 big areas

    Marketing narrative & leads
    Sales Process & execution
    Product Innovation
    Talent Acquisition & Nurturing
    Business Models
    Metrics & Measurement
    Fund Raising
    Risk & Robustness, Controls
    Acquisitions, Partnerships

    2. Be clear on the Performance Profile Expected (give me a few ideas for free may be fine)
    3. Reward structure

    Best, Ian

  • Guest

    great insight… i think its very important to develop a personal relationship between the adviser and CEO while at the same time keeping it within the confines of the workplace. This creates an opportunity for the two to share their opinions openly and decide on whats best for the business or project at hand

  • advantages of franchising

    I can say that this will be great advice that keeps eyes on your each and every detail. That would be great to visit here.

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