Should vs Wonder

(Person wondering in a field, by Diffusionbee)

I’m not sure the word ‘should’ is appropriate to use in a business setting.

Yes, I’m fully aware it would take a monumental effort to remove ‘should’ from our vocabulary. But that’s exactly what I’m suggesting.

Don’t take this to the extreme, I’m not against a simple ‘we should go or we’ll be late’. But in a meeting, brainstorming, or even casual watercooler conversation, I’m advocating for the removal of ‘should’.

Why, you may ask? Well, when someone says “we/I/you should do <something>”, it’s basically a command. And who wants to be commanded to do anything?

At most, if someone has a different opinion they will reply “I think we should do <something else>”. Where does that leave you… at an impass. At worst, they disagree but stay quiet, which certainly never uncovers the true best outcome.

‘Should’ leads to micro-management. ‘Should’ leads to people leaving. ‘Should’ leads to total destruction (OK, maybe a little too far).

Now, you may ask, what to replace this menacing ‘should’ word with? I wonder…

That’s right, ‘I wonder’ is a simple substitute for ‘should’ that opens a conversation rather than closes it.

‘I wonder’ poses a question that’s open to debate/feedback/comment. It’s the verbal equivalent to opening your palms rather than crossing your arms.

Nobody takes ‘I wonder’ as a command. Nobody views a boss saying “I wonder if this would be a good option” and thinks they’re a terrible dictator.

I had a board member who trained himself to ‘wonder’ all the time. Guess what, we had great open discussions about basically everything. I quickly started replying with a ‘wonder’ to his ‘wonder’… it was great.

So get a rubber band, put it on your wrist, and give yourself a good snap every time you say ‘should’ for the next few days. Then remind yourself to wonder. Extra credit for counting how many people wonder back to you.

Wonder more, should less… I’m guessing your conversations will be better for it.

Investor Reference Checks

In the past few weeks, I’ve witnessed startup investors being incredibly value-add and also seriously destructive. It always surprises me who ends up in which camp – my gut feeling is often wrong. There also seems to be little correlation between an investor’s value-add and seniority, background, or their fund’s ‘tier’.

The same can be said for the founders I work with. Trying to gauge the value-add of an investor feels nearly impossible during the fundraising ‘sales’ process (on both sides), and a founder backing out post termsheet because of a negative investor reference is nearly unheard of.

Something Kevin Kelly mentioned about reference checks (1) struck a nerve with me recently – that people are “reluctant to say anything negative” (which we all know) and to “elevate good behavior 10x more than punishing bad behavior”.

Kevin’s suggestion is to write a quick note asking to “get back to me if you highly recommend this <applicant> as super-great”

My first thought was that founders should write a similar “let me know if this investor has been highly valuable” email to a potential investor’s portfolio companies (2). That works fine on an individual basis, but the information is lost to the broader ecosystem.

Idea: send an email/message on the yearly anniversary of every investment round to every founder in the world, asking if each investor is incredibly value-add.

Then I thought, why not bake this idea into one of the many investor feedback sites that have launched recently? Or better yet, launch a new platform that simply asks “Is this investor incredibly value-add?”

No 1-10 ratings. No ‘Quite friendly’ or ‘They showed up late’ feedback. No investor rebuttal. Just the plain truth if an investor is incredibly value-add or not. Then display a ranked list of what investor has the highest number of founders who believe they’re incredible. Now that’s something I’d like to see.

(1) Bits of Advice I Wish I Had Known
(1b) Freakanomics Podcast

DUBNER: Here’s one that resonated with me in part because it’s very practical and in part because it has happened to me. You write, “When checking references for a job applicant, employers may be reluctant or prohibited from saying anything negative. So instead,” you write, “Leave or send a message that says, ‘Get back to me if you highly recommend this applicant as super-great.’ And if they don’t reply, take that as a negative.” Does that actually work? Do you know people who’ve had success with that method?

KELLY: Yes, I have used that method. There is a kind of a weird cultural moment right now where there actually are companies that cannot comment on previous employees and stuff. There’s a bias to saying anything negative for various reasons. But I have used this model of leaving a message on an answering machine earlier and now with an email saying, “Only reply if this person is super-great,” and sometimes I have not heard back anything. That’s a sign. And other times I’ve heard back, “Yes, you’re lucky to have this person.”

(2) Dear founder, I am considering taking an investment from <NAME>. Could you get back to me with a simple ‘Yes’ IF they have been incredibly value-add and you highly recommend them? If they are truly amazing and I’d be lucky to have their support, then I’d appreciate hearing from you.

The Components of Speed

I’ve always noticed speed varies drastically from company to company. Some are amazingly efficient, while others meander (or worse).

Recently, a founder asked me to help significantly increase their company’s speed. After a few conversations, we distilled the issue to focus and accountability. Basically, cut activities that don’t directly create value and stop accepting mediocre results.

I wonder, are focus and accountability the key drivers of speed at any company?

Are there other components of speed I’m missing? Do most companies consider how specifically to increase execution speed?

One aspect may be the mentality of team members; maybe some inherently execute faster and this company just has slow people? Or can anyone be fast when key company and leadership components are in place?

Basically, I’m left with more questions than answers. But I’m pretty confident speed is a leading indicator of a company’s success.

(1) Surprisingly it was a first-time request… seeing as how common the issue is

Me on the Iron Throne

Here’s one of my favorite slides from the “Going Global” session I hosted today with some amazing ScaleNL Dutch founders.

While some people present what they know, I basically overshare all the things I screwed up over the years… kind of like my version of group therapy.

I remember caring so much about consistency, brand, execution… when none of that really moved the needle compared to trusting and supporting the great people around me.

Hopefully reliving me on the Iron Throne trying to force people way smarter than me to ‘bend the knee’ will help others not make the same mistake 🙂

Cold Emails

I love what Stéphane and his crew at OpenVC are building, such an amazingly open ethos. They shared 14 actual cold outreach examples recently sent to VCs, all had the same general cadence:

Hi <VC>, I’m <NAME> with <BACKGROUND> building <PRODUCT> achieving <TRACTION> raising <ROUND>.

Anything feel off to you? Basically, all 14 are totally canned. And these were the best 😐 If you’re a VC, do these ever actually convert?

Email 5 at least writes “we feel like a great fit for <VC>”, but doesn’t qualify why with applicable examples.

Email 11 refers to a “chart on your website”, so at least there was a glance of research, but nothing further?

My guess is the amount of research/commonalities a founder refers to in a cold email directly correlates with their first call conversion rate:

Canned < 1%
Highly targeted > 10%

I wonder how many first calls an email like this would get…


Congrats on closing your fund <#>, I’m sure <INVESTMENT> must have helped – what an amazing company!

I noticed your post <POST> and investments in <Y> and <Z>, we seem to share a common interest in <INDUSTRY/MODEL>. In fact, I’ve been building <COMPANY> to solve <PROBLEM>, which I’m guessing you have some experience with as well…

Whatever else is written from here, as long as it’s concise, my guess is the VC would appreciate the outreach enough have a conversation.

If a founder puts this kind of effort into an investor email, just think what they will do to win customers, staff, etc. (or so a VC might say to themself).

Gratitude Coorelation

I’m making a few VC intros for a founder I rate highly, the replies:

A+: “Many thanks for the intro!”
A: “I appreciate you thinking of us!”
A- “Thanks for sharing the opportunity” (x2)
B: “Please introduce me”
B-: “Happy to speak with them” (x2)
C: “We will have a look”

I wouldn’t say the differences are huge, but next time I’ll certainly consider prioritizing the 50% who say thanks.

Interestingly, how appreciative the reply is correlates well with the ‘tier’ of the fund – the A’s are all top European VCs.

Interesting vs Critical

The hardest discussions to table are interesting, relevant topics that aren’t critical.

I find most meetings cover important topics in-depth, leaving critical ones for the last few minutes. Simple questions easily lead to everyone chiming in. Challenges are often listed, but rarely stack ranked.

This seems especially true for board meetings. Board members want their questions answered, and few CEOs feel comfortable tabling most questions… even if doing exactly that would accomplish the most.

Idea: take note of all non-critical questions and provide written answers within 3 days of a meeting?


A founder recently asked for my advice about creating hype and FOMO while fundraising, stemming from a post making the rounds in entrepreneur circles. Their take was…

“Based on the article, we should pretty much stop engaging with VC’s at the moment as we’re not (actively) fundraising, that information is a currency, and a certain amount of mystery seems key. Better to disengage entirely for the best chance of success?”

Something didn’t sit right, I better have a peek at this article – is it really suggesting founders not to engage with investors until actively fundraising?

Most of the advice is solid: a ’sherpa’ can help with introductions and navigate discussions, other investors suggesting a ‘hot deal’ creates urgency, craft your story based on current trends, don’t waste your time with tons of investor calls, be creative when attracting interest. Yep, that all resonates.

But this founder (and quite a few others, I’m told) focused on ‘intrigue is an asset’ as a key takeaway. If they plan every interaction, minimize casual interactions, and fill an investor’s mind with good news, then mystery and the magic of ‘limitless potential’ is created. Which then leads fo FOMO and ultimately investment.

In essence, unless you’re in total PR mode when speaking to investors, they’ll find out your company is a complete disaster and never invest in you.

To me, it felt like used car sales tactics more than finding a decade-long business partner and board member. But maybe I’m missing something? Perhaps the combination of planned, formal, mysterious, and good news is indeed the path to creating FOMO and raise a round?

So I called several investor friends (7 in total, all Partners of active VCs) and asked for their take on FOMO and relationships during fundraising. How did they source their best investments? How do they advise founders to fundraise? What % of their deals are FOMO related?

Instead of writing a slick post or creating an ultra-hip tweetstorm, I’m directly passing on the feedback I shared with the founder who initially asked for fundraising advice. It’s a combination of these 7 investor conversations and my personal experience. I hope it helps on your fundraising journey… may the FOMO be with you 🙂

1) Fundraising is about building a relationship over time, based on genuine/open/honest conversations (eg lines not dots)

2) The goal is finding someone you can spend a decade+ building with, who adds much more value than just money

3) Building investor relationships can have upsides other than fundraising, like introductions to potential revenue/staff/etc

4) Investors have seen it all (startup ups/downs), they see through planned ‘good news’ interactions (eg “the shit comes out in DD”)

5) A too much intrigue can set expectations too high, create trust issues, and even kill a deal that would have gone through

6) Instead of being ‘mysterious,’ think about frequently reaffirming the big vision (1/3) while sharing wins (1/3) and struggles (1/3)

7) Short term FOMO (eg mainly dark until fundraising) does happen in +-25% of rounds, vs 75% based on long term (9+ mo) relationships

8) This kind of FOMO is usually because of serial exited founders, incredible team, insane traction, or significant market change

9) FOMO fundraising can work, but there’s high risk if the market doesn’t form and you’re left with limited relationships to fall back on

10) When a FOMO fundraising ‘works’, it’s hard to push through IC, the dynamic can be off, and there’s limited rapport to work from

11) Optimal rounds are pre-emptive offers (with others then bidding), which entail some kind of dialogue and relationship

12) Treat fundraising like business development by segmenting your list into A) 5-6 top prospects B) 10-20 decent potentials, C) 40+ all other leads

13) ‘Massage’ deeper relationships with an A list YOU choose, vs 20+ surface exchanges with ‘time-wasting’ incoming interest

14) Spend time being top of mind with existing investors, frequent ambassador mentions to your A list go a long way 

Let’s address workplace bullying

Bullies suck. 

That kid at school who steals your lunch money. Or the one who calls you names. Or the teacher who shames you in front of the class… Yeah, bullies come in all shapes and sizes.

But what about bullies in the workplace?

Over the past week, multiple people told me they’re being bullied at work. They used phrases like someone is ‘challenging to work with’ or ‘has strong opinions’. But let’s be honest, in many cases it’s plain and simple bullying.

Let's be honest, in many cases it's plain and simple workplace bullying. Click To Tweet

A guy I know works for someone who uses their position of power to disparage him in front of colleagues and prohibits him from expanding his personal network (eg tying him to the job). To me this is bullying.

A woman I know had an employee ‘make friends’ with a senior colleague, then convinced this friend to spread rumors that she wasn’t a capable manager. To me this is bullying.

Another friend told me they felt obliged by superiors to stay out late drinking night after night while traveling for work. To me this is bullying.

Most recently, someone said their boss pokes fun of how they dress. To me this is bullying.

Child bullying both at school and online has been a hot topic in recent years. It feels like the public acknowledges the problem and has put solutions in place both to suss out bullies and support those affected.

Why hasn’t workplace bullying been addressed?

Don’t bully parents lead to bully children? Could we stop this vicious cycle at the source? Yet, how many companies even define what workplace bullying is, no less have a procedure to take action against bullying?

Don't bully parents lead to bully children? Could we stop this vicious cycle at the source? Click To Tweet

HR policies mainly focus on sexual harassment, bribery, etc – slightly more cut and dry situations. The subtle tactics bullies take to exert power, intimidate, or humiliate are difficult to report, but lay the groundwork for a toxic culture. They also often directly lead to more serious infractions.

Companies should have a plan in place to ensure their culture doesn’t accept bullying. Add an anti-bullying policy to your handbook. Include a question in your 360 reviews for bullying feedback. Highlight examples of unacceptable subtle bullying behavior during onboarding.

Most importantly, don’t treat bullying as two colleagues simply not getting along. Someone being bullied doesn’t want to directly ‘face’ their bully – that’s the problem… bullies are HARD to face! HR needs to directly address the bully, communicate the unacceptable behaviors, and set immediate corrective actions that if not followed will lead to termination.

Nobody should begin their day worried about being bullied. We seem to acknowledge this for children, now it’s time to move to the workplace.

Nobody should begin their day worried about being bullied. We seem to acknowledge this for children, now it's time to move to the workplace. Click To Tweet

Rewarding users for jumping ship?

I have been frustrated after being a long time user of a service and recently deciding to leave. When finally clicking the ‘cancel’ button, I have been taken to a screen like this…

In this case, I’ve been a member of audible for 3 years, paying a monthly fee and accumulating credits to purchase audiobooks. The day I decide to cancel my membership (huge backlog of books) is the first time I’m offered a discount.

How frustrating. It actually makes me feel like an idiot that I didn’t push that cancel button every few months for years – saving myself 50% every so often.

The same thing happened when I recently switched my phone plan. I had been an O2 (big UK carrier) customer for 7 years and never offered a discount. When I called to cancel, all of the sudden I’m offered 30% off for the next 18 months? Wow.

Why are solid long-term users rarely rewarded, while users who try to jump ship are offered a deal?

Why are solid long-term users rarely rewarded, while users who try to jump ship are offered a deal? Click To Tweet

It feels like retention marketing has become such a science, while incentivizing loyalty is almost never considered. How often have you ever seen a subscription service decreasing the price every year as a ‘thanks’ for being a valued customer?

SaaS company challenge: on your pricing page explicitly state that customers who renew their subscription after the first year will be offered a 5% discount.

Over a few days, do your initial signups increase? Do any other quantifiable metrics improve? I would guess at minimum long customer loyalty and positive word of mouth improve – two hugely important factors, which not coincidentally are some of the hardest KPIs to track.