Just ask

I’m not good at asking. 

Perhaps growing up in a large family over-sensitized me to come across as greedy. Or maybe pride gets in the way. 

I’m not sure. But I do know asking for what you want can open doors.

As a young guy, I was rewarded for hard work and solving problems. I learned that the bigger the mountain the bigger the reward waiting at the top.

Our adventure travel businesses were fueled by adrenalin, hormones, and ego. We attracted guides who loved to work hard, make everyone happy, and overcome anything the river, weather, or most demanding guest could throw at us. 

Whatever it took to make a tour a success, we delivered. 

With every business I started, I built on that foundation of head-down, if-you-want-it-done-right-do-it-yourself attitude. Even as my businesses’ grew and I added more staff I resisted asking for help.

I would work insane hours - often evenings and weekends. And instead of celebrating my team, I would feel resentment as they headed to the gym at noon, or packed their bags at 4:30 to go home.

There’s a story I heard years ago that perfectly captures this.

Walk on water

A man packs his bags and leaves his village to study meditation. Many years later, he returns, excited to share what he has learned with the local guru. 

“I have gone away for 20 years to study meditation,” he says, full of pride.
“And now I can walk on water.” To which the guru replies, “Yes, but the ferry only costs a nickel.”

When I decided to sell my last company I gave myself eight months. It’s a big job to turn a hands-on, entrepreneurial venture into a marketable business that someone else could own and run. You have to build systems, document processes, and strengthen your financials - all the while growing your client base.

For the first few months, I doubled down and worked long hours. On top of the demands of daily operations, I would try to find time to make the business sale-ready.

It was too much and I wasn’t hitting my targets. 

I remember thinking I needed to put in more time—find a few minutes here and there; and be more organized. It was the same old fog of pride and ego blinding me. 

It wasn’t working. So, I asked for help.

"If you want something you haven’t had you have to do something you haven’t done." T Jefferson

Inviting opportunity

Most of us hate asking for money. You might need money to bail you out of a tight spot, or maybe you’re asking for a donation to a local charity. Either way, asking people for money - or any favour - can feel imposing, like you are inconveniencing them in some way. 

Research in neuroscience and psychology shows that perceived social threats involved with asking—fear of rejection, signs of weakness or incompetence, burdening others, diminished status—activate the same primitive regions of the brain as that of physical pain.

While our reptilian brain might be lighting up, it turns out most people actually want to help.

A study led by Vanessa Bohns, a professor at Cornell University found that the rate people were willing to provide assistance (like donations) to strangers who asked for help was an average of 48% higher than expected.

Understanding that most people naturally want to help is the first step. The next step is to pivot from asking for help to offering an opportunity.

Offer opportunity

After a few more months of frustration, it was obvious to (thick-skulled) me I needed help. The deadline to sell the company was getting closer and all the work to get there was moving further away.

So, I sat down with my sole employee and laid my cards on the table.

Up to this point, I was heavily involved with all aspects of client sales and the client service process - from enquiry to product delivery. I always had been - like many small businesses I had developed relationships with most of my clients. But if I was going to open up more time, something had to go.

My invitation was for him to completely own client service - from the initial enquiry call to completion. This was a big deal. Once the sale was landed I was out of the picture—no longer would I have my fingers in client relations.

To help reduce his workflow, we would set up a simple reporting system for contractors to self-manage their workload.

Now, instead of new clients taking up many hours of my time with multiple touchpoints - especially when it came to solving their problems - I would spend 30 minutes on a sales call and move on.

This single ask turned into an immediate game-changer for me and a nice addition to his resume. 

We sold the business four months later.

"We are all social creatures with a long history of solving problems together. And that includes asking for help."

Asking is generous

We are all social creatures with a long history of solving problems together. And that includes asking for help.

I volunteer for a local society that manages trails in some of our more popular mountain bike and hiking parks. Our job is to cut back the brush, remove deadfall, and bring down dangerous trees. It’s hard, physical work, and incredibly rewarding.

When we head out as a small team we rely on each other to stay safe and to get the work done. And when one of us needs help heaving a log off the trail, or moving equipment we gladly pitch in because we want to help and it feels good.

We all need help in some area of life. And sometimes that little light in our reptilian brain will start flashing: “This might be uncomfortable!” “What if they say ‘no’?”

Do it anyway.

People want to help. Sometimes all you need to do is ask.

Here's a bit more reading about making good choices:

Humble Pie
The Spiral and the Flywheel
The magic of boring routines