Losing sucks
Recently, we lost a massive bid at Legal Engine, the AI business I co-founded. Eight months of work. Countless presentations, negotiations and 6am calls to Australia. An enormous amount of time, energy and emotional investment.
And we lost.
I’m still gutted. Still angry. Still disappointed. And, perhaps worst of all, still frustrated with myself.
Not simply because we lost, but because, looking back, there were things I should have done differently.
So, while the wounds are still pretty fresh, here are three lessons I’m taking away. Enjoy.
#1. Don’t put all your eggs in one basket
We did. And it’s come back to bite us.
The opportunity was enormous. Transformational. And somewhere along the way, it became all-consuming.
Other opportunities fell by the wayside. Conversations weren’t followed up. The pipeline suffered because we were so focused on winning the big one.
It’s understandable, but it’s also dangerous.
The lesson
No matter how exciting the opportunity, protect time for the rest of your pipeline. Ring-fence a few hours every week for prospecting, following up and nurturing relationships.
Because if the big one doesn’t land, you need something else to fall back on.
#2. When in doubt, trust your gut
Looking back, there were warning signs. Things we were being told by the delivery partners didn’t quite add up. Promises were made that didn’t sit comfortably with me.
My gut was telling me something wasn’t right. But I ignored it.
Why? Because I was blinded by the size of the prize. I wanted to believe what I was hearing, rather than challenge it.
The hardest part? I feel like I’ve let my co-founders down. At Legal Engine, we’re a small team. Everyone put an enormous amount of time, energy and effort into this opportunity. They trusted the process, and they trusted my judgement.
I should have challenged things earlier. I should have listened to my instincts. And I should have been more willing to ask the uncomfortable questions, even if I didn’t particularly like the answers.
There’s a fine line between optimism and naivety. I crossed it.
The lesson
If something doesn’t feel right, challenge it. Ask the awkward questions. Look for evidence, not reassurance. And don’t allow the potential value of an opportunity to cloud your judgement.
#3. Give yourself permission to be seriously pissed off
I’m not going to pretend I’ve bounced back with a spring in my step and a renewed enthusiasm for sales. I haven’t.
Losing something you’ve invested eight months of your life in is bloody hard. Particularly when you know you could have done things differently. Resilience in sales isn’t about pretending it doesn’t hurt. It’s about what you do next.
The lesson
Allow yourself to be disappointed. Then conduct an honest review. What went wrong? What was outside your control? What would you change?
Write down the lessons, make the changes and start rebuilding the pipeline.
You don’t have to feel positive to take positive action.
Chat to Tina by voice, when you’re between meetings, on the commute to/from work, or heading into something you’d rather avoid.
Final thought
There’s a temptation in business to celebrate the wins and quietly bury the losses. But I think we learn far more by talking about the latter. This one hurts. A lot. And it’ll take a little while to get over.
There’s more work to do, relationships to rebuild and more opportunities to create.
For those that chose to bin us, you know who you are. I’m coming for you. Until we meet again….
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