Hey #SMBtwit,

Have you ever thought about HOW you ask questions during diligence? I mean, really thought about it? Because how you ask questions matters, a lot...

🧵👇
You're all smart people. You're acquiring a business, so you know what information you need to look for. How you unearth the info you need is very important. You need to be strategic w/ your questions. 2/13
Let's talk about 'Walking the Stairs'. @ProfAWBrooks from @HarvardHBS does a wonderful job on this topic so hopefully, if I butcher this, she can offer some corrections... 3/13
There are two types of conversations - collaborative and competitive. Collaborative conversations are focused on relationship-building. Competitive convos are more zero-sum and transactional in terms of info exchange. 4/13
In collaborative convos, you should 'walk up the stairs' with your questions. Start w/ easy ones, escalating to more difficult as you build rapport, trust, and engagement during the discussion. Open-ended questions work well in this context – people are willing to share. 5/13
In competitive conversations, and diligence meetings often qualify, both parties are anticipating difficult and pointed questions. If you start w/ the easy ones, it may actually increase anxiety and frustration since everyone knows what's coming. 6/13
In this case, starting with the hardest questions and 'walking down the stairs' is often a better strategy. There's another reason this can be a more productive strategy in competitive circumstances. And it relates to something called the Recency Bias. 7/13
Recency Bias gives "greater importance to the most recent event" - it's why closing arguments in a legal case are so important. If you start with the most difficult questions and end with softballs, you can imagine the following conversation after the meeting... 8/13
"Wow, that got off to a rough start when Jessica dove right into the weak Q4 numbers. But you know, once we got past that, things got a lot better. The wrap up was great and I feel like we're in a good spot with this deal." 9/13
Despite the potentially contentious questioning at the beginning, finishing on a lighter, more positive note takes the edge off and leaves the impression of a good conversation. That's recency bias at work. 10/13
Now, asking tough questions ALWAYS carries risk, whether it's a collaborative or a competitive conversation. Use your EQ and behave accordingly. Also, as a buyer of an #SMB, any given meeting may be both competitive AND collaborative in nature. 11/13
After all, the buyer will often need to work closely with the seller during a transition and/or beyond, so yes, it's a negotiation, but it's also relationship building. Use your judgment about what style of questioning you want to employ. 12/13
To wrap up, it may be comfortable but don't assume starting with easy Q's and walking up the stairs to the harder ones is always the best strategy. In some cases, particularly competitive conversations, getting the tough questions out of the way can lead to better outcomes. 13/13
If you found this valuable, I could use the followers! Please like and retweet! 🙏

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More from @SteveWiesnerSMB

Jul 2
I wasn't smart enough to get into an Ivy League MBA program.

But I did.

Because I failed.

👇
I've always been an aspiring entrepreneur. I started a driveway sealing business in high school. Tried to launch a small sportswear concept in college.

But heading into my senior year I started a business that changed everything.
I went to college two hours outside of Toronto. Kids would head back to the city every weekend, but getting home was pretty painful.
Read 17 tweets
May 29
Yesterday's golf tweet got this Twitter noob some much needed followers, so will post one more.

My dad used golf to teach me a huge life lesson.

Well, several actually.

🧵👇

1/9
Despite growing up in Canada, my dad was a great golfer. The other side of scratch kind of golfer. To me, he was Lefty long before Mickelson. In his later years he tried to get his senior PGA card. He was great.

2/9
One day, he took me and my sister to play. I was 14 or 15 at the time. As always, I was hacking and he was killing it. Frustrating, yeah. I developed some golf rage back then. And that was lesson #1 – golf can bring out the worst in people and it certainly did for me.

3/9
Read 9 tweets
May 19
I had a client ask me if I love what I do yesterday. 🧵👇
My reply: “Thhhhhhatttt’s a good question. Do I love what I do? Hmmmm.” At first, I was rattled I didn’t instantly respond “Yes!” I mean, shouldn’t we all be 100% jazzed about this SMB life we’ve chosen? Did my pause reveal something? (2/7)
It did reveal something. The road less travelled is less travelled for a reason. This s*it is really hard. I’ve been grinding for a decade, and it’s still a struggle. Payroll, admin work, licenses, all the ticky tack things you need to do – stressful and not very fun. (3/7)
Read 7 tweets
May 18
Why will this recession be different than 2008 / 2009 for SMB? A short 🧵👇.
Tech has been democratized. There’s an app to streamline or automate so many processes. And if there isn’t, there’s an opportunity to build a low code / no code solution. Automation drives cost savings and scalability, and it’s accessible to even the smallest of SMBs. (2/5)
We live in a global village. A dr’s office in Topeka can hire a virtual assistant in Cebu to handle admin tasks. Companies like @Enshored can help. SMBs can find and qualify cost-effective resources, wherever they may be. This can be a life saver in tough times. (3/5)
Read 5 tweets
May 17
As an #smbtwit newbie, wanted to introduce myself. Short 🧵👇.
Born and raised in Canada. Moved to US for grad school. Then to bulge bracket IB (DLJ / Credit Suisse) to do M&A and sponsor coverage in NYC. (2/8)
Move to SF in 1999 to join the tech M&A team. Always infatuated with tech and saw some of the craziness at the end of the dot com era. Then, DLJ got acquired by Credit Suisse and I became a member of the CS tech team – a powerhouse practice. (3/8)
Read 8 tweets

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