Start begging for forgiveness

We’re at an interesting point at FreshBooks. We’ve grown out of my parents basement, into our third office where we’re expanding our footprint. From Joe and I in 2003 we’ve grown to 40+ people cranking away. Along the way we’ve blown through many stages, and now we’ve come to another one.

While we don’t have a strict top down culture, one of the things I’m finding is we have more of a top down than I ever imagined or ever intended. The solution? My new mantra: “beg for forgiveness, don’t ask for permission”. I don’t want people asking me, “here’s what we are going to do, what do you think?” I want to shift the conversations to “here’s what we did”, so I can ask, “what did you learn?”.

Obviously judgement is needed as there are some things the CEO should be notified in advance, and the truth is I still wear a couple hats. That said, I trust my team to make those calls.

So…we’ll see how it goes. But if you are building a business and find yourself here, ask your team stop asking for permission; ask them to beg for forgiveness.

9 thoughts on “Start begging for forgiveness

  1. […] This post was mentioned on Twitter by Rayanne Langdon and Ben Vinegar, Adam Park. Adam Park said: “@BusinessApps: Start begging for forgiveness #erp #smallbusiness” – Insightful read indeed! […]

  2. I like it :)!
    It is an interesting transition as FB grows to stay out of execution mode and empower others to do so. Making yourself less ‘available’ for that conversation will only enable people to try this on even more.
    The point of what did you learn is a strong one – that’s really empowering and fosters entrepreneurship, creativity and faster fail cycles which seems to be good. As you say, the trick will be the balance, that’s what strong values and a culture will ensure stays right.

  3. I’m a fan of companies like FreshBooks. I spend 4 years studying Computer Science at UofS, a few years back I returned to my home country and am doing a web startup myself now. FreshBooks is one of our inspirations, I recommend it all the time, Cheers!

  4. Mike,

    “Cisco & Freshbooks CEO Face Similar Mangement Challenges.” (say what?)

    Interesting post. Came across your website, blog researching Cisco/Avaya (my former company) and their SMB market push. Particularily into 1-9 employees = 900,000 in Canada (82%) as you well know. The SOHH market.

    fyi John Chambers, CEO has the same challenges and has adopted many of Gary Hamels “management 2.0”
    “collaborative” process VS “Command and control”.,4

    Of course with 66,000 employees who have to be reprogrammed to “act- then ask”, verdict is still out on the final results. (20% of Mgmt left the firm over last 5 yrs. (ironically many went to Avaya). Actually, MOST employees are looking for “C&C”, if they weren’t they’d most likely start-up their own parade).

    Links to Gary Hamel, Cisco here;


  5. Mike McDerment

    Very cool Stuart – thanks for chiming in.

  6. Mike,

    Sounds like you’re starting to make the transition from startup to expansion stage… Which involves lots of changes in the operating focus of the CEO. Very exciting…

    Check out my blog, which I write with my audience being the expansion stage software CEO. I hope you will find some of learnings useful.

    In particular, I have three posts I call “The CEO Imperative”
    Building a Cohesive Senior Team
    Focus on the Few Things That Matter
    Set the Annual Rhythm

    Would love your feedback…

    Good luck,

  7. […] Mike McDerment and his co-writer Donald Cowper address in this book is an age old question for developers, how do […]

  8. […] Mike McDerment and his co-writer Donald Cowper address in this book is an age old question for developers, how do […]

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