How would you describe your last 365 days? Was it what you expected from the professional and private standpoint?

It’s not a surprise that life is full of unexpected twists of events. We can surely agree that, in one way or another, our plans are always complemented with a series of astonishing events.

The length of the period we’re observing is of little significance comparing to our willingness and aspiration to reflect upon often and on just about anything we do.

An advantage of the aforementioned astonishing events is that they stimulate action. Those events are uninvited indicators hinting that the actual outcome is unlikely to be aligned with our expectations and that some of the existing conditions need to change.

Regardless of what part of the software development industry we’re in, the unexpected events should lead us to the conclusion that transformation has already started and we need to act upon it.

Differences in perception create opportunities

Rapidly growing companies understand the importance of moving swiftly, being agile and reflecting often. They tune their instruments and adapt to the fast-changing, technology-driven economy as quickly as those changes and transformations emerge. There is always too much to do and way too little time to do it.

Looking back and reflecting on recent periods competes with other priorities, creating an illusion that it can wait until other pressing issues are sorted out. However, it’s often those little findings and clues that make the most significant difference in the way we build our company’s future and competitive advantage.

On the flip side, the employees’ perception of company culture and performance may drastically differ from the leadership viewpoints. The best of the leaders invest their time in understanding the talent and intellect that drives their businesses.

Do we understand our employees’ desires, hopes, needs, fears, or personal impediments? Do they feel comfortable taking ownership of their piece of the puzzle that moves the company forward?

Good retrospectives are based on trust and safety

The entire agile ecosystem relies on reflection to change, or retrospective. When enacted appropriately, retrospective is a fantastic tool that helps discover the essential ingredients we should maintain, improve, remove, or embrace. It’s a simple concept, but often challenging to get right.

Retrospectives are a well of incredibly useful information and a platform for making some of the most important decisions. Success depends on setting a comfortable environment where the quietest of the participants will feel good about sharing some of their most intimate feelings about the company and teams they work with.

Leading such retrospective workshops, my work depends on creating the appropriate environment where individuals will have the opportunity to relax and feel safe. With the help of a few exercises, they lower their guard to expose their feelings, thoughts, concerns, and hopes.

Typeqast is one of those rapidly growing startups where culture is continuously redefined as the team explodes in size. A custom-tailored retrospective I recently organized for them depended on my ability to create a safe and fun atmosphere. Instead of discussing the company’s services, we focused on storytelling. Marking events and impressions on the Typeqast’s timeline allowed the employees to take full ownership and embrace the power to identify the company’s strengths, gaps, opportunities, and threats among all the layers of the company structure.

With a clever combination of transparency and anonymously disclosed feedback, we can reveal extremely valuable insight. Some of it is upsetting and conflicting. In other cases, this insight inspires and influences. Regardless, it’s necessary that we provoke action.

Every company has a soul created by the same people who create the company culture — the employees. As with any organism, some challenges are unique, but many are shared with companies alike. Coming from the startup world, I learned that many companies suffer from issues that follow similar themes as they work hard on obtaining greater agility through transformation.

I realized I should share the key learnings with anyone else working to grow their company and at the same time cope with the challenges transformation brings. I can’t promise these will apply to your situations but may at least encourage you to take a step back and consider reflecting at your company’s essence.

Sales misaligned with delivery

Sales teams are mostly incentivized by success bonuses, which may decrease the quality of prospects in favor of volume. In return, this practice often generates toxic clientele, work that pays at a terrible expense to our talented teams. The toxicity is a product of misaligned goals, unrealistic expectations, and the lack of understanding of the scope of effort needed to complete the work successfully. This problem alone is the most frequent of complaints I hear in retrospectives.

Good organizations have the tools necessary to protect their teams from toxic clients. Prominent organizations identify such clients in the pre-sales phase.

Uncontrollable growth

Culture is at risk when growth is explained in headcount. It’s hard to grow fast and hire the people who are going to fit well with the existing culture. In fact, diversity is the best thing that can happen to a culture. However, an evolving culture can be walking in a minefield unless healthy communication is enforced on all levels. This problem multiplies when experts are promoted to managers, albeit missing adequate training in managerial skills.

Retaining talent

Off-peak periods can offer exciting opportunities for the company and its talent. Employees love the ability to do something special after a period of extensive work is over. Such examples may include learning some something new skills, R&D, pursuing certifications, etc. Those are always a valuable investment, but some companies tend to avoid such investments due to the sheer cost of it.

Some companies go to the extent of letting people go, especially contractors. In most cases, acquiring and onboarding new talent is far more expensive than investing in the personal growth of the existing employees.

Overwhelming scaling of professional services

Services don’t scale well. There’s only so much that people can do with their time. Due to an increase in sales, companies take work they cannot support, so they stretch the employees thin.

No matter how hard the leadership tries to invent new ways to improve productivity with multitasking, teams do best when focused on one thing at a time.

Deteriorating organizational structure

As companies grow the organizational charts, tend to remain outdated. Agile organizations know that org charts are never set in stone, supporting the premise of continuous transformation. The goal is to pave the way to where we want to be in the foreseeable future, instead of where we are right now.

As the structure adapts to our growing business, are we being transparent about it?

Many of the leaders I worked with were surprised to learn that their employees had no idea who to turn to when they faced problems in the workspace, personal issues, questions about professional growth, or even when they craved feedback. Mechanisms that offer such employee support are usually in excellent shape to maximize the benefits of retrospectives.

How we structure our organization can be a strong push forward or a dangerous threat to the sustainability of internal culture and the ability to carry out the vision. No single organizational chart perfectly closes all the gaps and suites everyone’s expectations. Retrospective is a powerful tool that helps iron out the bumps in an org chart by detecting pain points, verifying previous decisions, and setting the cornerstone for transparency.

Your turn…

Don’t confuse leadership with dictatorship by making communication a one-way street. Good leaders understand the concept of servant leadership and are capable of being good listeners. Such leaders are on a great path of converting from the challenged to the challengers, learning from the good, the bad, the disturbing, and the extraordinary.

Have you recently attempted a retrospective? Do you feel it was set up to maximize input from the participants? Can you identify with any of these findings and ideas? Do you have different experiences? 👉🏻 Let me know in the comments below.