Dragons’ Den Interview With Brian Epstein

Dragons’ Den Interview With Brian Epstein

As featured on Dragons’ Den

I was recently interviewed by Dragons’ Den for my expertise on working with friends. Here is the article they published.

Working with a friend seems like a logical and fun proposition. A friendship at work (a “workship,” if you will) can come in many forms — hiring a friend, working for a friend or becoming partners. Having someone in the workplace that you already trust and like can give you a morale boost and an impetus to get some good work done. However, for all its benefits, turning a friendship into a workship can have its risks. Any business association can get complicated or strained, but when it’s with someone you’re already friends with, it can quickly test both ends of the relationship. That’s why it’s crucial to know what qualities to look for in a potential friend-turned-colleague, how to set boundaries and the best ways to manage any conflicts so the partnership can thrive. Here’s how.


Likability is key for a friendship, but it’s merely the tip of the iceberg when working with friends. Whether you’re a friend/boss or a friend/employee, it’s important that you both share core values. Career management and leadership coach Brian Epstein believes the most crucial values in a business relationship between friends (and any business relationship) are integrity, commitment, emotional intelligence, passion, trust and reliability. Beyond this, you should both be able to roll with the punches. A word of warning; if you seriously doubt some of these key values in your friend, it may be best not to work with them.

Is your sibling also your best friend? Epstein also warns that it’s perhaps “a good idea not to bring family members into the business fold,” since familial relationships often have less flexibility than normal friendships.


Establishing clear responsibilities and expectations from the start can prevent a lot of the more common conflicts that arise from working with friends. Epstein even suggests putting together a sort of “prenuptial agreement,” with a “complete understanding of the skills, experience and strengths that each person brings.” This agreement should detail the workload both topically (what each person is responsible for) and time-wise (monthly, weekly, daily), as well as preferred working styles (eg. your friend/boss prefers to have scheduled meetings rather than an open door policy). Be as transparent as possible by outlining your weaknesses, concerns and future ambitions (e.g., determine whether the friend you hired is planning on making this a temporary stepping stone or a long-term position). Remember, this is not an exact science and this agreement can always be subject to review and revision. If possible, you may even want to begin your new partnership with a trial period where you both get to test drive the arrangement and establish clear guidelines from there.

And as your new workplace relationship takes off, you should anticipate a change in your old dynamic. You can’t always be buddy/buddy in a boardroom and you may pull back on the social time you spend together outside of the office because the work time has increased — and that’s okay. Being flexible while adapting to this new relationship will do a lot to ease growing pains.


Any workplace friendship is bound to have its rough patches, and that’s where your guidelines come in handy. For example, if you’re being overworked by your friend/boss or if you feel like your friend/employee is not pulling their weight, referring to the terms in your initial agreement can keep the discussion from becoming too personal, and that is key.

“Conflicts should be about the business,” says Epstein, “no personal attacks should ever happen.” When working toward a solution, Epstein hopes each individual will be willing to talk and listen to the other person’s perspective in a diplomatic manner while using “I” statements to express their concerns. He believes other colleagues can also play a helpful role in tough situations like this, so it may be best to “invite outside opinions and judgements where possible to keep work scenarios unbiased.”

But a friendship-turned-workship is not all doom and gloom because, even in conflict, working with a friend can have its advantages. Don’t overlook the fact that since you started out as friends, you’re already comfortable with each other and you know how to communicate, even when it means tackling tricky situations.

It’s elements like this that can make a workship worth it — but only if the aforementioned values, clarity and adaptability are firmly in place.

Originally published on the CBC’s Dragons’ Den