Share The Scary

October 29, 2023

The Value of Presentation Transparency: And How It Scares Most People

In this article, we’re going to talk about a scary topic: the ‘scary, hairy’ secret you may have with your business.

Maybe you have a business that looks excellent to the outside world, but your unit economics are currently a struggle.

Perhaps you have excellent unit economics and an excellent business strategy, but are still working to solve your pipeline conversion to generate revenue.

Or perhaps you’ve solved the pipeline issue but you’re concerned that your business’s competitive landscape may ‘appear’ congested to an outside viewer.

Whatever the thing that keeps you up at night with your business: the truth is that no business is perfect.

So what should we do with our ‘proprietary’ piece of scary information?

Conventional wisdom and everything in your gut is going to say to hide it.

However, in this article we’re going to talk through why you should share your ‘scary’ secret outwardly, how to consider sharing it, and most importantly, how that might – counterintuitively – benefit you.

The Context: A Quest For Outward Perfection (Thanks, Social Media)

In the current day, there’s a lot of pressure on startups and consequently their Founders: It’s easy to see highly successful Founders, thriving in their businesses online:

  • Tremendous revenue here
  • Large exit there
  • Having the time of their life over there

With the ‘manicuring’ of businesses and the difficulty of succeeding as an entrepreneur, when the game is focused on presenting the perfect picture, no one wins. The original businesses positioning their businesses perfectly will be perceived as not pragmatic, the newer businesses will see the ‘bar’ and feel the need to match, and there’s an endless upward, falsely vain cycle. Investors (or sponsors, or whomever) don’t win either as their role to assess businesses is made more difficult while trust is broken down.

Surprisingly, a similar scenario goes for Corporate workers as well. Make your job look amazing. Others see it, feel they fall short. Others feel the need to show the good side only. Recruiters (or companies) lack transparent information and have a more difficult job to do. Similar cycle.

So How Do You ‘Win’ In This Cycle?

In the current transparent, social-media-driven environment, your natural inclination is going to be that you must meet this standard.

However, your presentation viewer – be it an investor or a strategic partner or even your boss – likely has material business experience and maturity. Translation: they know that there are at least some challenges that you have in your business. And even more than this: each of these constituencies is likely there keen to help you. To help you learn. To help you clear obstacles. To add strategic value and feel like they have some influence over the opportunity you’re leading.

And this is even further magnified in a world in which trust is materially broken down – by false outward appearance.

Ok So I’m Listening, So What Are The Benefits Of This Scary Approach?

Ok so we’ve at least partly convinced you of taking the ‘unnatural’ approach to sharing about your business. So perhaps let’s amplify the opportunity that exists here to truly see the benefits you’ll receive from this approach:

  • Perceived Sophistication & Poise: The ability to demonstrate that you understand the nuance of your business, its operations and the wider industry/macro context, shows that you’re a strong steward of your business. Additionally, it shows your pragmatism; your understanding that there will always be obstacles to solve, that you’re aware of them, and you’ll seek to solve them.
  1. Better Customer Experience For Your Viewer: Remember that person viewing your presentation? Yeah…they’re your ‘customer’ here. Your job: make their lives easy and add delight. Make it easy for them to absorb, demonstrate all of thought that you’ve put in, and equally importantly, delight them with your openness and thoughtfulness. What’s not delightful? Your audience having to ask uncomfortable questions or having to fish for information. Make their lives easier.
  2. Built Trust: Pretty self-explanatory. Tell the truth, share the current situation, build trust. Sure that may lead to a filtering of those uninterested or slightly more unfavorable terms to reflect the risk, but you want a business partner who is motivated to help you as well. Think pie-expanding, not pie-stealing.
  3. Differentiation: Simply put, not many others are doing this, enabling you to further stand out from your competition. See: first two sections above.
  4. Additional Thought Processing (& Maybe Even An Answer!): Another opportunity to discuss a challenge is another opportunity to process it. And another opportunity to process it puts you closer to finding a solution, especially when discussion with different-thinking individuals is involved as well.
  5. A Comfortable, Clear Conscience: Perhaps a bonus benefit, but you’ll also likely feel more comfortable and confident that you can share openly where you have challenges. This ‘look yourself in the mirror’ test while not necessarily directly impacting your business’s result, is sure to impact how you feel about yourself and the way that your company does business.

Where Does ‘The Truth’ Go? Do We Put It In Our Deck? And WHEN Do We Share It?

It’s worth calling out that there is of course such thing as ‘sales’ and positioning. You most certainly need to demonstrate the positive differentiators of your business.

With calling out your business’s ‘obstacle’ or concern, there are three primary methods that you could take:

  1. Data-Driven Balanced Approach
  2. Assertively Preemptive Approach
  3. Back-Pocket Approach

The Data-Driven Balanced Approach implies presenting information in a transparent and consistent manner. This presentation intentionally doesn’t try to ‘over-impress’ but presents information in a pragmatic, very linear manner. Pros: Balanced thoughts equally spread throughout, poised/elevated sentiment. Cons: Lacks marketing pop.

The ‘Assertively Preemptive Approach’ seeks to very actively call out the issue at hand (as well as preemptively address it. By way of example, this could be demonstrating the ‘awkward’ competitive landscape, but also displaying why you have a unique insight or sustainable differentiator that will lead your business to success. Pros: Exciting spin/differentiation, strong contrast. Cons: Potentially a bit marketing heavy, ‘emotional-feeling.’

The ‘Back-Pocket Approach’ is a pre-prepared response to any question you’re likely to receive in polished form. In this approach, you may not include the challenge directly in your core presentation, but you’re also not hiding it either – perhaps proactively even seeking to demonstrate the slide to address a concern that you (and your audience) may have. Pros: Linear flow of your presentation with attention on excitement. Cons: Delayed ‘trust’ built, potential for not having time to discuss challenges openly.

Ultimately, the recommendation we have is to tailor your approach based on two primary dimensions:

  1. Your personal (and business’s style)
  2. Your audience and what you think their preference may be

However, in any case, do not be scared to share openly about your business.


In this article we talked through the counterintuitive principle of sharing your business’s challenges. In the current world – be the application for a startup or even a corporate opportunity – there is a tremendously ripe opportunity to be open, to build trust with partners who you wish to work with for years to come.

Ultimately, how you approach being transparent will come down to your strategy; however, in all cases: a) certainly continue to show the positive aspects of your opportunity b) definitely come prepared to all aspects including the challenges and c) be proud of your business and not too hard on yourself.

Good luck and we look forward to hearing about your success, from ‘unconventional’ approaches or otherwise.

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