Every kind of leader needs two kinds of support if they want to lead well and produce results. 

1. Technical advice or mentorship 
2. Thinking partnerships 

So why might you want technical advice?

We need technical advice when we don’t have experience in a certain area. It’s why boomer parents ask their kids (and grandkids) for help with their iPhones. It’s why new founders want the advice and counsel of former successful founders. 

Technical advice is helpful because it allows you to tap into the experience and wisdom of someone who’s gone before you. They’ve made some mistakes and learned some lessons that you can use for yourself. 

But technical advice has pitfalls, like survivorship bias. 

Yes, this person was successful but you usually don’t know that much about why they were successful. It could be that they were brilliant, savvy, and strategic, but they also could have gotten lucky. Usually, success is a mix of skill and luck and the challenge is that you don’t know how much of their success was based on luck vs skill. 

In the extreme, it’s like asking for advice on how to win the lottery from a lottery winner. The winner might have a method but that method doesn’t account for much. So when you seek out technical advice or mentorship this is something that you need to account for. 

Another challenge is the context gap problem. 

Different things tend to work in different contexts. And the likelihood of something (a strategy or a tactic) working again correlates to how close the new context is to the old one. 

That’s why you’re likely to get the best advice on how to build a table from someone who has built lots of tables. You could also get advice from someone who has built chairs and the advice will probably still be decent (because chairs and tables are pretty similar). But if you ask for advice on building a table from someone who carves small statues out of wood that advice may not be very helpful. It could even be harmful in some ways. And while this is obvious it becomes more subtle as your increase complexity. 

When it comes to businesses and startups the context can change in a lot of different ways. The market is never the same, the investor pool is different, the industry has matured, and government policies have shifted. 

So even when the context is similar you’ll always have to filter for these changes and adapt the advice based on your situation. Because while technical knowledge and mentorship are a total game changer for most people, they can also give you some bad data when you’re trying to chart a path forward. Especially if you over-rely on it. 

So that’s the power and challenges of technical advice and mentorships. 

Now let’s talk about thinking partnerships.

There are a bunch of ways to create thinking partnerships but the two most common are masterminds and coaching. 

Both of these work in a similar way. 

• You bring a problem or challenge to the table
• The person or group asks questions and reflects what they see
• Through that process, you clarify your thinking
• You come up with novel solutions or experiments
• And you get access to blindspots and insights that are hidden in the process itself or your thinking about the problem or opportunity. 

The best thing about thinking partnerships is that they help you think better, be more creative, and they tend to help you grow more personally than mentorships. 

The big reason for this is that they push you to reflect on yourself and your thinking and as a result, you can’t help but begin to notice patterns of thinking that might be holding you back. 

The main downside to thinking partnerships is that they mostly rely on your previous knowledge and experience in order to help you make better decisions and gain better insights. 

If your assessment of the situation is wrong or there’s something obvious you’re missing, they can lead you down the wrong path. Then again thinking partnerships aren’t as subject to the cognitive biases of mentorships. 

Because the purpose is robust thinking and personal development you tend to base your decisions and strategies more on what’s happening in your situation rather than on some past model that no longer applies. 

So which one should I hire? 

If you want to be successful you tend to need both. 

You need someone with experience that can help you avoid making mistakes but you also need thinking partnerships that help you grow and develop your ways of thinking about the business or project you’re running. 

Here are the questions I usually have people ask when they aren’t sure whether to hire someone who is an excellent thinking partner but lacks subject area knowledge or if they should hire someone who is an expert in an area but may not be as good of a thinking partner. 

1. Right now how many of your challenges are technical in nature? –

Let’s say you’ve got a software problem at your SASS or your code is bad and you don’t know how to fix it. 

If you primarily have technical challenges, working with a technical guide is better. But if your focus is on things like leading people well, enrolling key stakeholders, or clarifying a vision then a thinking partner would be better. 

2. Can you get technical guidance someplace else? –

Ironically I’ve found it’s easier to get technical guidance (for free) then really good thinking partnerships. The internet is filled with advice and people love giving advice. As a result, you can usually find information about the industry or problem you’re working with. 

What I’ve seen is that growth is usually not stopped by a lack of experience but an inability or unwillingness to try various tactics and approaches to solving a problem. I’ve also found that finding someone that really helps you think better and who won’t just give you advice is much harder. 

If you can’t get technical advice easily on the challenges you’re facing then go hire someone to give it to you, but if you can get some advice or support from well-known sources or a trusted mentor you’re going to be better off working with a well trained thinking partner like a coach. 

3. Are you stuck on a lack of knowledge or a lack of action/enrollment? –

If the big barrier to moving forward is knowledge or risk mitigation hire an expert. It will be worth the investment.

BUT if there are things you know you should try and you aren’t or can’t get your team onboard then you probably need a thinking partner. Because these kinds of challenges tend to be a result of approach or style rather than a lack of data or experience. 

4. Is it better to get the right answers or ask the right questions? –

If you need answers to key problems this is when technical guidance can be a great shortcut, but if you’re not asking the right questions thought partnership tends to be better at framing problems in new ways. 

Another way to think about this is, Are you trying to learn the standard way or develop a new way? If you want to know how things have worked expertise is better, if your focus is innovation thinking partnerships are better. 

5. How important is short-term growth/results vs long-term growth/personal development? – 

If you want or need results in the short term experts are great! In fact, they are often much more reliable than thinking partners in the short term, because they know what will work the fastest (assuming the context is similar enough).

But if you want to grow yourself as a leader, hone a culture, or gain insight that your team can use for a long time, thinking partnerships tend to be better. 

The reason is simple. Thinking partnerships ask you to do the work of thinking, considering, experimenting, and learning. Because you don’t take a shortcut, you learn more about the journey and the territory you’re in. It may be harder in the short term, but there really isn’t any replacement for personal experience which is why thinking partnerships are so potent. 

Still, sometimes you need to make changes fast and adjust quickly so urgency is an important factor to consider. You can create fast results with a thinking partner, but an expert might be able to give you a guide to what’s worked before so you don’t have to reinvent the wheel.

Final Thoughts:

In reality, you need both of these things if you want to achieve your goals. You need to learn from others experiences and you also need to develop your own way of thinking. 

If you rely too much on experts your thinking isn’t as creative or innovative, but it may be easier to get started. And if you rely too much on thinking partnership and ignore the inputs of experience you might risk falling into common pitfalls. 

The bottom line is that you need to find a way to have both. Some founders use their investor networks to tap into experience and hire a coach to help them with their thinking and growth. Other founders, leaders, and entrepreneurs hire consultants to give them valuable expertise and then form informal coaching or mastering relationships with their peers to hone their thinking. 

No matter what you’re approach is it’s important to not neglect either side of this equation. A great coach or thinking partner is usually harder to find (though you can find ok thinking partners with more ease) and will help you grow much faster than you if you just work with experts or try things out yourself. But experts are incredibly valuable for solving specific problems and helping you learn without making mistakes yourself. 

So don’t settle. Get creative. Find amazing thinking partners AND get the advice you need. Don’t choose between the two simply find a way to experience them both. 

Love, 

Toku