Eleven insights from eleven years in business

With a certain football match being played just before Obelisk’s 11t h birthday, our CEO Dana Denis-Smith couldn’t help but reflect on team work, belief and the will to win. Here are her eleven insights on what it takes to be a pioneer, drawn from eleven years spent changing the world of work in the legal industry. Happy Birthday Obelisk Support!

#1. Execute on your plan

Believe in why you started in the first place, irrespective of what others say. At Obelisk, we have always believed in longevity in the legal profession and that careers should not be cut short by pressures at home. Too often talent is wasted due to outdated stereotypes; we set out to challenge that thinking and we always will.


#2. Go at your own pace

My child was born within the first year of the business, before we managed to win any meaningful business for our model of outsourcing work to home-based lawyers. This meant that for the first 3 years I worked around the child’s needs. It gave me incredible insight into our lawyers’ lives and how they too could work around other commitments. I was even more convinced this could work with the right support for them from Obelisk.


#3. Always stay curious

I didn’t come to creating a solution based on the view that I knew best. I always start from the point that customers know best what their needs are and it’s our job to find new ways to deliver what they need. Too often curiosity is stifled by busy-ness or hierarchies, especially in the legal world.


#4. Build the team you need to win

I have had amazing support over the last few years. So many people I reached out to, out of the blue, extended advice that was incredibly valuable. We’re so lucky at Obelisk to have built an amazing community of consultants, customers, colleagues and champions that support us and each other.

“I didn’t come to creating a solution based on the view that I knew best. I always start from the point that customers know best what their needs are and it’s our job to find new ways to deliver what they need.”

Dana Denis-Smith

CEO, Obelisk Support

#5. Put the work into being a pioneer

If you’re first with an idea, you have to put the effort into educating the market. Helping customers see how they can do things differently can lead to them becoming more aware of their choices and options. Sometimes that might mean it’s not your business that gets picked for a project. I can live with that, knowing that we’re driving real change in the legal industry.


#6. Don’t believe the hype

Innovation must be the most used word in the legal industry but the reality on the ground is very different from the conference hall buzz. Too often restricted budgets and a conservative leadership approach mean new ideas can’t flourish. Courageous leaders don’t fear testing new waters and underlining the change with spend. Most of us in the NewLaw space are here today because of early adopters that were brave and took a punt on us. We need to keep going and continue to push the boundaries as the novel becomes commonplace.


#7. Celebrate progress

Seeing how much women in law have broken through over the last ten to fifteen years is amazing. I am privileged to have played a part in championing this with the First 100 Years – spotlighting role models, our history and why we belong in all the rooms where decisions are made. I have so much faith in the generations coming after us to build on what we have achieved.


#8. Show, don’t tell

The pressures of being an entrepreneur are great and with every stage of new growth something changes and you need to keep pace; culture is built top down. What kind of leader you are will set the tone for the team to follow, which is crucial when your business is growing so fast.

“Seeing how much women in law have broken through over the last ten to fifteen years is amazing.”

Dana Denis-Smith

CEO, Obelisk Support

#9. Never be afraid to take a decision

There are so many crossroads we come across in business. You have to have self-belief and be decisive. Success really requires you to have a short memory of failure. Sometimes the solution you have is too early or not clearly understood but you will always learn.


#10. Invest in flexibility

I’m passionate about encouraging flexible thinking. Whether it’s adopting flexible working, pivoting your business model or flexing how work gets done in your legal team, putting a little bit of time and effort into enabling more flexibility in your business always delivers a return.


#11. Always put people first

I know legal tech is all the rage but without a strong team and trust in people most things fail. All that we have achieved is due to the people who believe in our purpose and mission and are human first.

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