5 conversational ways to evaluate great consultants

Startups and more mature businesses alike, and those large and small, at some point will need to hire a consultant or two. Want to get the best bang for your buck? Ask some tough questions!

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1. Make sure they’re not going to quit

I’ve heard so many crash and burn stories over the years, it makes my head spin.

One client had hired a consultant who was supposed to be the best in NYC. After only a few weeks of working with the client, he explained that they were “doing it all wrong”. Furthermore he had a travel schedule to meet, with speaking engagements in South America.

So he basically dropped them! As the client retold this story to me, I wonder if they could hear my head shaking, I was stunned. Who would turn away from a customer in pain? And furthermore turn away from one who could clearly use the expertise of someone who had seen a lot before!?

Keep in mind the reasons why people leave consulting.

2. Be sure they have some war stories to tell

Any consultant who’s been in business for a while, surely has some good war stories to tell. Talk about those, and find out the battles they’ve been in.

I can tell a few myself. In one case I was only 12 hours from leaving for summer vacation when a long time colleague and former client called me. They were in a serious emergency. The big boys, the remote DBAs that many in the industry use, had broken their database. Replication was misconfigured, and they were running blind. I ended up on a SKYPE call fixing the database and troubleshooting problems on Virgin’s inflight wifi. You don’t forget that kind of firefighting.

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Be sure they won’t quit, ask about war stories, test for some push back and be sure they empathize with your business pain. But more importantly ask them to tell their own business story. You’ll learn a lot.
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For another client, back in the dot-com days, their application was stalling completely. Customers were leaving, and so was an 80 million dollar buyout deal. Nothing a few Oracle parameters couldn’t fix!.

And there are always a few tales of woe between sales teams, and the engineers that then must deploy solutions in the real world. Beware the sales wolf in sheeps clothing and do your homework aka due diligence on technical solutions.

3. Ensure they can provide resistance & push back

Good consultants have to walk a tightrope all the time. On the one hand they are tasked with making their clients happy. At the end of the day, improving their position, business bottom line, yes these are crucial. Sure that means saying yes, that means trying to be a problem solver as much as possible.

But always saying yes, avoids hard truths that you have to share. I had one client whose primary Oracle dba went on vacation. Before he left we reviewed systems. Multi-master replication in Oracle is brittle by nature. We both agreed. And I agreed not to change the configurations lest it break other things down the line. Not one week into his vacation a mandate comes back from on high, this change absolutely has to happen now. There are millions of dollars at stake!

Applying strong resistance is necessary to avoid breaking something even bigger. And it was not easy to stand strong in the face of such pressure. But I assured the team that such changes would mean even bigger problems for the company.

4. Find out if they empathize with your pain

In one of the biggest ironic twists, consultants should understand the pain of building a business. Because they themselves have experienced when clients don’t pay so they understand cash flow problems themselves. That is what every small business struggles with, and most startups too!

5. Ask them how they built their business

For me, one of the least appreciated things about independent consulting is, that in the most important ways, it is about running a small business. So someone who has built and kept running a freelance or consulting business knows how to make hard decisions, and keep their eyes on the ball.

A consultant needs to know how to get business first and foremost. But then how to manage engagements carefully. Once you’ve got those two down, keep building your business incrementally.

Someone who has successfully run a real business for years can share the story of what they’ve done. What has worked, what hasn’t worked, how they have pivoted when necessary, how they have failed fast, and moved through it.

They can tell you how they stay cash flow positive, can deliver on time, can be likeable and communicate with teams, and really understand every side of a business.

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