Managing Forward

John Cousins
March 4, 2023
6 min read

Managing forward, also known as managing expectations, is the skill of setting and communicating realistic goals, targets, and timetables. This is important so that harboring overly optimistic expectations doesn’t disappoint others.

Managing expectations is an underrated skill. We need to be aware of, and develop it as a skill set, so we can avoid a lot of the drama that goes on in every office, and in our personal relationships.

Emotional drama engendered from disappointment impedes our ability to focus on and accomplish important tasks. Things get delayed, derailed, and mired in minutia. Not managing expectations well can be very costly.

The value and importance of managing expectations can be seen in the markets. Value is lost in public company stocks when analyst and investor expectations are not met.

Promise Less, Deliver More

Leaders who are adept at managing expectations are able to more seamlessly navigate the obstacles of their business and personal lives. They know how to communicate, organize, and direct conversations to focus around getting things accomplished. When expectations are not met, or perceived not to be met, leaders lose credibility and projects lose momentum.

Here are some strategies to improve your ability to manage expectations.

Don’t Make Assumptions

And be aware of the ones you do make. Have you heard the one about Assume? When you assume, you make an ass of u and me. Ass-u-me.

Don’t fall into the trap of assuming someone has the same understanding of a situation, project, deadline, or task that you do.

Avoid this snare by having a conversation in which you openly and explicitly discuss what’s expected, how it might be accomplished, and how success will be measured. Our vision of the future is cloudy at best and we need to remember to communicate the various contingencies that we are aware of and also explicitly acknowledge the possibility of unexpected issues arising in the future.

We should develop strategies about how we will deal with the knowns and the unknowns. Always discuss alternate plans and develop possible work-arounds. Allow people to contribute and entertain alternatives as a way to get buy in.

Leave plenty of opportunities for questions. This is the time to agree and commit to what will be delivered, and when. When something is going to be completed is one of the most common points of miscommunication.


Make a point to communicate with everyone involved frequently. Err on the side of over-communicating in the early stages of a new project or as a key milestone or deadline approaches. Low stakes conversations can eliminate surprises and help mitigate and address problems and issues.

It may appear to be time consuming more work, but it’s especially important if you have a new team that isn’t used to working together or new leadership that may not have developed a level of trust in the team’s ability to deliver. If people feel included and aware of what is going on, they are less likely to feel ambushed by delays or budget issues.

By frequently checking in throughout the course of a project, you also have the chance to provide real-time status updates and manage any delays, risks, or contingencies.

When something unforeseen develops and becomes apparent, report it ASAP. Don’t try to buy time and hide it and hope to fix it before anyone finds out. Being honest and upfront about a delay is way better than promising to deliver and missing your deadline.

Set Realistic Expectations

Expectations need to be realistic and achievable. If you don’t feel the ones that are being set are realistic, you can, and should, push back. This is a negotiation. The key here is refine them in a way that acknowledges the organization’s needs and balances those with the team’s abilities.

People don’t want to know about potential setbacks and there is an implicit incentive to over-commit so as not to rock the boat. Do not give in to this temptation to please. Confront the uncomfortable realities up front. Acknowledging limitations, and being open about what can be delivered and when, instills confidence.

This is important when designing marketing and messaging materials and is especially pertinent to on-line businesses like downloadable digital products and apps. When designing and launching minimum viable products you really need to communicate what the feature set is and manage expectations of what customers are receiving.

Speed to market is crucial and conventional wisdom has it that if you aren’t a bit embarrassed by your initial offering then you waited too long to launch. When people are paying you money for something and they don’t get what they expect, that’s when they reach for the refund button.


The challenge when managing expectations boils down to managing two variables:

1. Communication

2. Preconceptions

People have different preconceptions based on their experiences and they will use past experiences as a benchmark for what they expect from you.

Communications and Memos

Taking the time to craft explicit written directions can ultimately save a lot of time and wasted effort. Inefficiencies arise when instructions are misinterpreted, not heard, or understood incompletely. Written communications help minimize this pitfall.

Management by Email

Many people disparage email as impersonal and lacking in communication cues like eye contact, tone of voice, and body language. There is certainly truth to these criticisms but the medium’s asynchronous nature and its transcendence of space more than make up for the its shortcomings.

Email is a great management tool. There is not a lot of wiggle room for interpretation of directions and tasks when they are written. It is great for disseminating to groups, and the discipline required of writing forces you to be clear in your request. Your directives are or should be explicitly laid out and clearly documented.

Emails preserve fidelity of communication, whether directed to a group or based on from person to person to person as a message is forwarded. We are all familiar with the old game of telephone where someone starts with a phrase and it is whispered from person to person until the last person says what they heard and then the initial person says what started and everyone laughs at the difference: Purple Monkey Dishwasher!

Avoid miscommunication. Email communications help avoid this trap.

But a word of caution: Do not become the servant of your email. Use email judiciously and continually root out unimportant sources of email.

Tim Ferris has great advice about how to help you ruthlessly rid yourself of distractions. Low priority tasks dilute focus on big impact activities.

Focus on being efficient and combating procrastination. Tim also has good advice for email habits, including not to look at email too often, use spam filters and the unsubscribe function to weed out extraneous junk mail, use auto-respond for repetitive responses, and delegate to assistants who can handle day-to-day reactive email activity.

Ferris goes so far as to say try looking at email once a day, once a week, or even longer, which might seem extreme but ultimately frees us up for more important tasks at hand.

Share this post
John Cousins
Author, Entrepreneur, & Teacher

Receive my 7 day email course

Take your finance skills to the next level with my 7-day corporate finance email course. You'll learn all the essential topics from financial analysis to risk management in a fun, engaging format. Each day, you'll receive an email with practical examples, exercises and resources. Perfect for aspiring finance pros or anyone looking to expand their knowledge. Get ready to transform your finance game!

By clicking Sign Up you're confirming that you agree with our Terms and Conditions.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

If you like this article. Here are some more articles I think you might like.


The Road to Becoming a Unicorn: A Quick Guide to Startup Funding Rounds

The whole process of funding and developing startups has become more widespread because the cost of getting a product to market has dropped so precipitously in the past couple of decades from millions of dollars to typically anywhere from under $20,000 to $500,000.
John Cousins
December 18, 2023
7 min read

Oh Behave! Behavioral Economics: Why we do what we do.

Behavioral Economics is a method of economic analysis that applies psychological insights into human behavior to explain economic decision making.
John Cousins
December 18, 2023
4 min read
Personal Growth

Professional Development: 3 Types of Skill Sets

To perform effectively in a job and advance to greater responsibilities requires developing a well rounded set of skills. Every job and every industry has its specifics but these skill sets are general and apply across all jobs. Skills are fundamental for turning a job into a career trajectory and this trajectory is part of our personal fulfillment in life.
John Cousins
December 18, 2023
5 min read