Just ask questions to say what you mean

First time founders juggle a lot of different stressful topics:
Not running out of cash, keeping the team focused, not losing control of the board, sales plan etc.

Each is an art from and requires patience and inner-strength. Its also easier said than done, when you are surrounded by stress and pressure of competition and so on.

One thing that I hear from many first-time and young founders, is their utter frustration with their team. This comes across when the founder confides in me and says “they don’t get it” or “what a bunch of…”

Now, most teams are made of good and talented folks, who are taking a big risk in joining a startup. So why the frustration?

Just like no one will care about a child more than its own parents, the same is with a startup. The founder/s are the parents and they care and worry about the baby by design, more than anyone. More than board members and investors.

The advice I give founders about handling cases when they want to yell at their team is simple: just ask questions to say what you mean.

Again, easier said than done. If you want to blow off steam and suck the oxygen out of the room – go ahead do it. However, you will also need to waste a lot of time to bring back the atmosphere to where it was before your rant.

If you have that time to waste, then you can stop reading this post… now.

To keep the team motivated, even when mistakes are made – I advise you to adopt the Socratic questioning method.

What does that mean?
Say that you were promised by the team software will be written and tested for a big client by Friday. You get to work on Monday to find a flame email from the big client that says “Where is the software you promised me Friday???!!!”

After you face palm yourself, and begin to feel the frustration coarse in your veins – you need to decide between:
1) Get the team in a room and tear into them
2) Do nothing
3) Get the team in a room and ask questions

Now, I planted #2 here for fun – so I hope you did not choose that option.

Option 3, on its surface seems to be lame, and not matching the severity of the situation, your frustration level and overall the “panic” the team should be in. Right?

Nonetheless, if you pick option #1, you are not guaranteed to get the results you want either. Say that you picked #1 and gave the team a piece of your mind…
You may feel “better” afterwards by thinking to yourself “I showed them! they know who is boss now… what a bunch of…”

Yet, you also sown fear and intimidation – which may be the very cause of the software being written and tested without the focus you NEED your team to have. By the very method your chose to “fix” things, you actually made things worse.

Think about that.

You may have also began a set of unintended consequences which may lead to good people looking elsewhere for a job.

Here is a sample dialog, between a founder and the team, that ONLY has questions in it, not a single accusation. At the end of it, you can decide if the intensity of the situation was addressed or not.


Boardroom meeting – Monday 12pm
Attendees – Founder and team

Founder: Team, I received this email from our big client, have you all had a chance to read it?

Team: Yes

Founder: I want to understand why we did not deliver the software on Friday, as we told the client we will. Can someone help me understand the chain of events?

CTO: I was told last Wednesday that we need to code and test this software, and deliver it by Friday to the client. We worked on this all night, and were done Friday at 6am.

Founder: Sounds like you pulled an all-nighter for this, which I appreciate. Can someone tell me what happened next?

QA Lead: I got an email at 9am when I got in Friday, that the software it ready for testing. I knew we were supposed to deliver it tested by end of day Friday. My team started testing, and we hit a snag. So we went back to engineering and they fixed it right away, and then we began testing again. We finished testing at 7pm Friday.

Founder: Sounds like you and the team took this seriously, and did whatever it took to deliver on time. Did you then send the software to the client?

QA: No, that is our customer success job, to be in touch with the client and make sure it worked for them. Our job ends when we finish testing.

Founder: Is there someone from customer success who can tell me why the customer did not get the software?

Customer Success Lead: I personally sent the software after it was tested to the client, and still waiting for them to tell me if they need help. I sent the email to them Friday at 8pm.

Founder: So you are saying, the software left our building on Friday at 8pm, close enough to when we promised it. Yet, today I get this flame email from the client. Can you verify which account we sent it to and that its not stuck in your outbox?

Customer Success: Ah, you are right, let me check. It looks like I do have an email stuck in my outbox, but its not this one. In my sent items folder I see the email leaving my account at 8:02pm on Friday and went to John Doe, which is the correct account I was told to send it to.

Founder: Hmmm… that is odd. Then how come the client is pissed off and writing me this flame email? Anyone has an idea?

(murmurs in the room)

Intern: What was the size attachment we sent them?

Customer Success: 9.2MB zip file

Intern: and you have no bounce message about size limit?

Customer Success: No

CTO: Let me check our email server logs… I see an email at 8:02pm but it was not sent… it was blocked by our outbound filters. Let me see why. The error says that we block any.zip attachments automatically, as this is a common way for malware to exfiltrate data.

(silence in the room)

As you can see, you can uncover a lot of things by simply asking questions. The tone was not raised in this meeting, no accusations made, and a methodical “post mortem” analysis is taking place instead.

At the end of this story, the Founder asks the team to post the software to a cloud storage, and asks the big client to download it from there while they are still on the phone. After the client said a non-thankful “thanks”. the founder asked a question.

Founder: Would you like to know what happened?

Client: Sure

Founder: We sent an email on Friday at 8pm with this file, but our email outbound filter blocked it for security reasons. Its not an excuse, yet, I do want you to know why it happened, and that we take security seriously here.

Client: You know, we had the same thing happen to us the other week, and we found out that we did not block the file from leaving – but the recipient email rules blocked it as suspicious. We sent it with a .zip extension which raised some red flags on their end. I know how it is, and I wish email filters had less false-positives.

Founder: Especially on important emails… junk I get just fine.

Client: Exactly. Thank you for sharing what happened. At first I thought your startup is not up to the task, and you are too small to work with us. I know understand what happened, and I know it could happen to anyone. I hope no one lost their job over this…

Founder: No, we gathered the team to conduct a post mortem and discovered what happened. By asking a lot of questions you can…

All this to say, that you can get things done, learn about your process defects without rattling the cages. Learn to ask questions, and have the team learn through the process.

As after all, getting angry is punishing yourself for the mistakes/stupidity of others.