Airship is a small company (currently 40 crew members strong!). However, no matter the size of your organization, transparency is key to creating a culture of truth and ownership in outcomes.

As you lead your company, you must take it into your hands to normalize transparency early on so that as you scale this habit is part of your core. At Airship, we do this through our monthly Flight Path and Crew&A.

You can typically gauge a company's success by how quickly they make decisions, right or wrong. This shows cohesiveness and trust of the team but also the understanding that failure is part of the learning experience.

Outside of having an amazing team, there is a key aspect of decision-making that is just as important: transparency within the organization.

To make decisions you need data and to get on board with decisions, which is important for executing what’s decided, you need to provide the information that allows your team to connect with those decisions. 

I wish I could say that I communicate decisions and changes of strategy extremely well 100% of the time. It’s just not possible with a diverse team of individuals. However, as the leader of the organization, this is a job “only you can do.” That’s why you must create space for everyone to submit questions and concerns, anonymously or identified, around decisions and, most importantly, stand in front of the organization and address those questions and concerns for everyone. Likely the person who asked isn’t the only one curious about the topic. Having this safe space to address items is critical to your culture, the efficiency in which you execute, and the overall success of your organization.

There are two ways in which we create space for this, one is proactive and the other is reactive. Again, you won’t communicate effectively 100% of the time the first time so make space for those that need a bit more clarification after the fact. 

Proactive: Flight Path

You should be running your organization on some sort of metrics. These metrics are likely different between industry and organization but they are important to keep visible to track success on a weekly and/or monthly basis.

To ensure that our Crew is up to speed on our trajectory, I plan a Flight Path review at the end of every month to create space to share how we are doing toward our 1-year goals and how decisions impact that trajectory. For us, this is a simple Google Slide deck shared in our last weekly Crew Meeting of the month and includes these metrics:

  1. YTD Revenue
  2. YTD Expenses
  3. YTD Profitability
  4. Monthly Billability (how we track billed work)
  5. 1 Year Picture Comparison - Ground to Cover
    1. Revenue
    2. Profit Margin
    3. Closed Deal Value
    4. Hiring and Retention
    5. Larger Projects we are tracking to 1 year.
  6. What’s Next? This is where we talk about decisions that are being made to impact the reviewed metrics positively. 
  7. Questions

That’s a lot of information but it’s very intentionally delivered. Now, our Crew knows where we need to improve and we cover how each position can positively impact these. However, as you can imagine, these numbers don’t make sense to some and questions don’t always come to mind in the window to ask them. This is why there is Crew&A.

Reactive: Crew&A

Whether it’s metrics from our Flight Path, concern around a team change, or if we are ever considering an acquisition, you must make room to address the items in your team’s heads. We do this by having a monthly Crew&A meeting where I (or others more equipped to answer the question) address the questions submitted with the entire team. We have three rules, 1) no questions are off-limits and 2) answers are as direct as the questions, and 3) we always allow time to discuss at the end of the answer. This has led to some of the most impactful conversations and process changes for our organization. This is not always a comfortable meeting, there are real questions with real topics that aren’t always easy to answer. However, for me, the harder the better because I have found that those have led to deeper trust and shined a light on some blind spots that will make us better. 

Opening up the floor for your team to ask anything can be a little uncomfortable at first. Either you’ll get softball questions or you’ll sit there in silence because no one feels comfortable submitting. Here are some tips to get started.

#1. Set the Tone

First, you set the tone. As the leader you should have some pulse from the team through direct interaction or your leaders should be bubbling that up. With that knowledge, you should be the first to submit a question. Do it anonymously and make it a hard one. Then the team will see what’s allowed and how you react to those tough questions. 

#2. Fill the Gap

Always have something to talk about if there are no questions or if you get through all of the questions before time is up. I typically bring 3 items that are on my mind as the CEO because I am not immune to assumptions myself. I will bring these up for discussion to fill the space.

#3. Set Expectations

Set proper expectations around how questions are answered. Sometimes there are 2 questions and sometimes there are 10. You mustn’t rush answers and leave room for discussion so I always communicate that we may not cover all questions and if we don’t get to one it will roll over to the next Crew&A. As importantly, don’t start answering a question with 10 minutes left in the meeting, this causes adverse communication, just save it for the next one.

#4. Be Prepared

Prepare answers ahead of time so that you’re not fumbling for the answer during the call. Tripping over words or rambling can present a posture of being untruthful or not confident in the answer. You must be confident in your answer even if the answer is “I don’t know but I will find out.”

#5. Share the Mic

You don’t always have to be the one that answers. This is your meeting, you facilitate it, but some questions are better answered by other leaders in your organization. In the preparation time, share the questions with your leadership team and determine who is going to answer that question, and ensure they are prepared to do so. There is an additional “pro” to having others answer, it shows the trust at the leadership level and the humility that even the CEO doesn’t have all the answers all the time.

Questions or concerns left unattended, leave a gap that can only be filled with the assumptions of those who hold them unless you create space to correct that. Assumptions can and will be influenced by that person's current state of mind. As a leader, one of your jobs is to ensure that transparency is normalized and those unattended items have a spotlight of truth poured on them. A proactive and reactive approach is the one-two punch I use at Airship.


Start with: What problem are you trying to solve? 

One of the activities we work through revolves around refining your problem statement. A problem statement is the key business problem that needs to be solved. In software development, it states “what has to be done” for a project to succeed. It does not say, “how it has to be done.”

We use the 5W’s + 1 H format as well as the SMART Framework when establishing a problem statement. In fact, you can draft your own problem statement by using our free download. This download will get you thinking through some of the questions and answers prior to starting your project.

Download: Problem Statement
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