Tell it like it is: Managing Expectations for Entrepreneurs


Tell it like it is. This is easier said than done. 


It’s a challenge for many entrepreneurs to manage expectations. They are usually unstated but are critical to a startup’s success.

People often manage expectations poorly because of a fear of lowering standards. There is an urge to prolong a state of delusional happiness until it is absolutely necessary to face reality.  Managing expectations is time-consuming, easy to procrastinate and sometimes very uncomfortable.  However, despite the initial discomfort, setting the right expectations prevents awkward conversations, builds trust and may also save a business!

There are 3 pillars of expectations that every entrepreneur must be aware of and be able to manage.  First is to yourself, next is to your family and friends, and finally is to your customers and investors. These are critical to achieving the end goal and launching a sustainable business.


Managing your own expectations is the first step.  Optimism signals confidence, abilities, perseverance and positive outcomes. These are clearly the traits startup founders need to get their first customers, funding or boost employee morale. Sounds great doesn’t it?

There are two potential problems, though. When harsh reality kicks in, the zealous entrepreneur may not even realize it, or casually brush it aside. Secondly, there is such a thing as too much optimism. Really, a launch plan in a month and there is no prototype? Or really, the price of the product is less than the cost of its components? The only person an entrepreneur is fooling him/herself!

The best precaution: find a mentor, advisor or a board of directors who will tell it like it is to ensure that you are grounded in reality!

Family and Friends

No one can deny that starting your own venture is like a roller coaster ride, but those closest to you probably have no idea that they are also in for a stomach-churning adventure.

As you embark on your entrepreneurial journey, you, and your friends and family need to be prepared for internal turmoil and drama. Your only certainty is no paycheck, no steady income, no fixed schedule and no predictability. Everyday something in the news, on acclaimed publications or trending websites, may send dismay up and down your spine. Whether it is a new well-funded competitor launching the same product as you, or perhaps an expert claiming that your industry is dead, this isn’t a ride for the weak or complacent.

Don’t forget to strap in your friends and family for the journey! It’s going to be a bumpy ride.  You have to continually keep them in the loop, and make sure your loved ones take their (e)motion-sickness medicine.

Customer and Investors

The bottom line is that it’s tough to deliver when and what you planned for your customers and investors. Your launch may take you twice as long and cost double the pennies, and that’s the best-case scenario. Schedules are shifted, budgets are rebalanced and the original scope is tweaked, prodded and pivoted. However, you are in good company – even our favorite fruit company recently delayed their phone shipments.

Don’t fall into the trap and announce a premature launch.  Potential customers and investors can see right through that and it will be challenging to save face when the truth comes out.

To keep projects and employees on track, check out BaseCamp, or if you’d like a tool with free access, DeskAway. Both are cloud-based solutions that you can use immediately. Allocate tasks to your whole team, check on the status in real time and keep track of a lot more. These are all baby steps to keeping aware of your true progress.

Good luck as you strive to under promise and over deliver on the road to entrepreneurial success.  What has been the toughest part of managing expectations for you? Share in the comments below.

About the author: Kriti Vichare

Kriti Vichare is a marketer, entrepreneur, and cartoonist. She is the illustrator and co-founder of #entrepreneurfail, a web comic about the ironies of starting a company.  She is also the founder of IdeaKube, a company that facilitates brainstorming through ‘ideation parties’.  Kriti was a former marketer at PepsiCo and Kraft Foods. You can connect with her at http://about.me/kritivichare.

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