Decision-making vs Execution: Whats the difference between being a contrarian and being misaligned?

The people in every organization I have been in have had some recalcitrance to saying what is on their mind - especially publicly.  Tools like TinyPulse and Lattice try to create ways to give feedback anonymously, and that is useful. All feedback is useful. But feedback is most useful when it is vocalized face to face.  Then a conversation can happen. The more people in your organization speaking their minds the better the decision making.

Why do people fear speaking their mind?

There is absolutely a power dynamic at play. That is something management needs to be good about acknowledging in order to create a transparent, risk-taking culture and I wont get into that in this post (though it is very important). Beyond that, and the crux of this post, is a misunderstanding of what the expectations are for folks in the decision-making phase vs the execution phase.

So why are some employees celebrated for being contrarian and others are seen as renegades? It comes down to when the employee is pushing back and then ultimately in how that manifests in their execution. Understanding when decisions are being made and when they have already been made (and it is now time to execute) is key to understanding the distinction.

Before going forward, I want to state, that differentiating decision making and execution is a skill and knowing how to be a persistent contrarian in decision-making processes is a super power. It is not necessarily intuitive. So while the concepts can seem easy, in practice they can be tricky to apply, but learning these skills is a must for management and other strategic roles.

Decision Making

First, let's talk decision making. Making decisions is very important, especially for small companies. In a small company, changing tack is pretty easy, but hesitation is deadly (as I blogged about a while ago in "Does your organization make decisions?"). In all organizations, decisions need to be made in order to move forward, but startups specifically need to make decisions more than they need to make the right decisions; if that makes sense.

Decisions can be big or small. Top to bottom or bottoms-up. They can be the color of a button or the purpose of your organization. All of these decisions need to be made, with the bigger the decision typically having a longer decision making cycle and often require more people to be involved.

As an employee, it is key to understand when the room is in a decision making phase. In this phase, it is incredibly valuable to be a voice of dissent, even as just a 'devil's advocate".  This input can help shape the decisions being made and help the organization make better decisions. This can be a super power for an employee and can quickly garner notice from the top of the organization and lead to promotions into management or other strategic roles.

Decisions need to be made. Decision-makers in a company are doing their best to make decisions with the data available to them. Often times these decisions are wrong.  It's important to keep prospective and know that the most important thing is that decisions are being made, communicated and executed on.


Without the right communication, nothing happens. The tricky thing about communication is that in the early days (when the organization is small) communicating decisions is pretty much free.  Decisions are made as a company, and context is easy to come by. As an organization grows, communication becomes more costly. It is not uncommon for decision-making to be the easy part and communicating the decision being the hard part (and requiring more time and effort to do well).

While working remotely, it makes sense to regularly document and share out decisions using Slack or email. Once you are back in an office, make sure to start putting rigor around communicating decisions whenever you add a layer of management.  Every layer of management will require additional effort to communicate decisions.


Once the decision is made, it is time to execute on that decision. With a lot of decisions being made, you will often need to "disagree and commit" which is an essential tool for any executive or strategic leader. Dissension is key in decision making but alignment in execution is 100% necessary for a functional organization. As organizations get larger it becomes more common than not for any given employee to be executing on decisions that they don't 100% agree with. That is okay and as organizations and remits grow, providing input into many decisions but deciding on few of them is to be expected.

When the organization is executing it is no longer productive to debate the decision that was already made. Down the road, once something has been tried, the decision-making window opens back up and a new path may be set, but while in the execution phase, not following through on the decision means that the decision was never attempted and the desired learning and output from that decision will be unlikely to materialize. With many folks in an organization, some executing and some not, the organization will flounder and eventually fail. This is the most common type of organizational dysfunction.

I want to note that within executive teams or leadership circles, it is not productive to harp on past decisions made by a colleague. Chronic poor decision making is noteworthy and should encourage exploration by leadership, but I want to caution against introducing conservative decision making or decision-making paralysis by persistently criticizing decisions already made. Disagree and commit means letting past decisions go and looking toward the present and future.

During the execution phase, the focus is on execution, driving alignment and learning.  Anyone in an organization can help in driving alignment. In organizations that have recently grown or where the team fabric is just being knit, there will be gaps in the communications of decisions. In this case, identifying these gaps, seeking answers and proactively sharing information on a decision will help drive alignment during the execution phase. This type of behavior is highly valuable. Also, while executing, think about feedback as objective reporting: Removing any priors, and focusing on dispassionate observation or "What am I witnessing right now?"  That will feed into future decision making.

Where relationships between employer and employee get fraught is in the Execution phase: A decision has been made, and for whatever reason, the individual is not able or willing to carryout that decision. Sometimes this is a failure to communicate, and assuming the best intentions of others is the best first course of action. But in cases where communication can be ruled out, then the individual is likely misaligned with the decision and by extension the organization. To an observer, this may appear as if their colleague is just voicing their dissent, but what is actually of concern is a lack of execution on a decision already made.

Many times, a failure to execute by an otherwise competent employee is a conscious or subconscious recognition that they no longer believe in what the organization is doing or the direction it is going in. To anyone experiencing this, that's okay! That happens all the time. If that's the case, talking through a way to exit is the best course of action for everyone involved.

Take Aways:
  1. If your organization isn't making decisions, thats a red flag.
  2. If there is a decision being made, speak freely.
  3. When a decision is made, execute your face off regardless of whether you think it was the right decision.
  4. Help drive alignment and provide observations (stated as facts) about what you are seeing during execution.
  5. Repeat 2-4.

Hope this helps! Bring on the dissent and then let's all get down to executing.

Trent Krupp

Founded Threaded: The personal rolodex built from your existing data. Previously, Head of Product at Impact, a market network serving the entertainment industry as well as Head of Revenue at Triplebyte and Hired. Founded an agency in my 20's, sold it to Hired and became employee 5. Recruited for VCs, growth and public companies. Helped the founders of recruitment tech startups, Trusted Health, Terminal and Beacon in the early days.