Breaking the Cycle: Unrealistic Planning in Software Development
Unrealistic planning in software development is a relentless cycle that teams and companies can fall into. It begins with setting ambitious plans without fully grasping the true costs involved. When these plans inevitably stumble, months have already slipped by, leaving everyone puzzled about where things went wrong. This cycle of planning, failing, and hastily moving on without learning from past mistakes is something I have witnessed a number of times in my career.
The Problem
In my career, I have often found myself in the midst of planning sessions and their follow-throughs, which tend to unfold in a predictable manner:
Teams across engineering, product, leadership, management, and stakeholder positions gather for a planning session. Sometimes the focus is on a single feature, other times on mapping out a quarter or an entire year, and occasionally, on launching a Minimum Viable Product (MVP).
Goals and deadlines are typically set, and in some instances, pushed forward by individuals who may not fully grasp the complexities involved in realizing the feature, plan, or product at hand. Driven by business and sales objectives, there’s a general expectation that the engineering team can bring these goals to fruition.
However, there’s a disconnect. Those in the know, aware of the real challenges, often hesitate to voice their concerns. Some are disengaged, tired from previous attempts to communicate their insights when their voice fell on deaf ears or was quickly shut down. They have witnessed this cycle repeat and choose to conform rather than confront. Others convince themselves the plan is feasible, not wanting to let down their superiors or appear uncooperative. So, despite the wrenching feeling in their gut that says “no way”, they remain silent and agree to do the unrealistic.
There is a third group in the room – those who are in the middle. They don’t have a strong opinion of what is realistic and what is not. Therefore, they are happy to just follow the multitude and help along the way. This group usually remains silent also.
The meeting concludes, the plans and timelines are set and everybody goes off with their marching orders. Soon enough hurdles and blocks slowly start creeping in. The initial momentum and enthusiasm are slowly and unnoticeably curbed. Progress slows down. Nevertheless, everyone is dedicated and hard at work. All delivery teams keep pressing forward. Finally the deadline is here but the deliverable is not. Some are disappointed, others are furious, others think that great progress was made given how difficult the effort was. The result is – more time, money, and effort is needed and a new deadline is established in hopes to hit it this time. In some cases, because new priorities have taken over, the effort is shelved for the time being, in hopes to finish it later. Many know that “later” will never come but there is nothing they can do. In other cases the project is deemed a total loss, costs are sunk, and the teams move on with new plans.
This repetitive cycle not only saps resources but morale too, leaving a tangled mess that is increasingly hard to clean up. Not to mention that overall forward progress becomes extremely difficult.
Overwhelmed by the cycle of ambitious plans and the reality of software development in your company?
As a Fractional CTO, I specialize in guiding tech startups and growing software companies through these exact challenges. My role isn’t just about overseeing technology; it’s about ensuring your team’s efforts align with realistic goals. If you’re in need of strategic, part-time leadership to help launch or scale your product, let’s explore how my Fractional CTO services can help you.
Ready for change? Contact me for a FREE consultation to discuss how we can make your next project a success.
8 Recommendations for Leaders
It is better to interrupt this cycle early on, before it gets out of control.
“An ounce of prevention is worth a pound of cure.”
― Benjamin Franklin
Give a Voice to Everyone
Create a culture where everyone can be heard, especially in a group setting. Make sure that titles and authority do not dominate the conversation, nor trump the opinions of individual contributors. Seek input from everyone in the room, and especially from those who rarely speak. Remember that many times the best thoughts and ideas come from those who don’t readily speak up.
Make it OK to be a Single Voice
Create a culture where it is acceptable to be the only person in the room with a different opinion. Sometimes, that individual might be the only one seeing the truth while others are unified in a contrary opinion. I have personally seen this happen more than once. However, if your company culture discourages or, worse, penalizes holding a unique perspective and being that lone voice, people will hesitate to speak up and share their genuine thoughts and concerns.
Be Willing to Hear the Truth
As the leader, be open and willing to hear the truth. Listen to those who are down in the trenches – the ones who are the builders of your product. Most times you will have your own opinion, but try to listen objectively and hear what your teams are saying. You may or may not be close to their day to day work. You may or may not be intimately familiar with their challenges. In either case, maintain an open view and, while having your own opinion, hear and consider that of others in the room.
Instead of Us vs Them – How can we?
During planning sessions tensions can run high, especially when leaders, managers, and stakeholders are told that what they are asking for is impossible in their desired timeframe. Those situations can quickly create a feeling of “us vs them”. It polarizes a company and divides it into 2 groups:
– Those who are business driven and feel like theirs, and the needs of the business, are not being met.
– Those who feel like unrealistic demands are always being pushed on them, despite their efforts to explain the reasons why a particular request might be unrealistic.
Be careful not to allow such polarization. Instead, unite the group and encourage creativity. Acknowledge the difficulty of the ask and invite the whole group to ask questions such as: How can we create the best result here? How can we creatively meet the business needs without burning out our teams? You might be surprised about the results that you will get.
Count the True Cost
Imagine someone telling you, “I plan to buy a house, but I only have enough for the down payment and the first mortgage payment.” You would likely think they haven’t fully considered the actual cost of home ownership. You might even question their judgment. So why would you launch a new feature or product without fully understanding its true cost, setting your team up for potential failure?
I have often heard people say, “Had I known what it would take, I would have never started.” This is something that most entrepreneurs will tell you. Here is the difference however – they signed up for something bigger than they thought, but despite the challenges pushed through and succeeded. We will all need to do that at times. The situation described above is – the cycle usually ends with failure and then repeats itself without new learning.
Learn From the Past
No one is perfect and every company will have situations where teams bite more than they could chew. The real challenge however, comes when the vicious cycle described above becomes something that is regularly repeated at a company. The compounding effects are massive and hard to dig out from. Therefore, it is important to catch these cycles early and change them into more productive planning sessions.
Stand in the Middle of Reality
I once heard a quote that a Product Manager used to say regularly: “We must stand in the middle of reality!”.
What is your reality? Are you willing to acknowledge and accept your reality as it is and not as you wish it would be?
Change your strategy, plans, and behavior accordingly, based on what is truly happening, in order to get better results.
Understand where you have been and where you are going.
“What got you here won’t get you there.”
― Dr. Marshall Goldsmith
Don’t be Greedy – Decide What is important
Where I grew up we have a saying: “If you try to sit on 2 chairs at the same time you will end up on the floor”.
Let me finish with a personal story:
As a landscape photographer I like to go out in nature and capture beautiful scenes. I regularly chase the right light and weather conditions in order to photograph a beautiful image.
Years ago I decided to shoot a winter sunrise in the mountains. The location was about 1.5 hours away and I had to be there well before sunrise, if I stood any chance of catching the right light. Therefore, I got up around 4am, drove in the dark, parked my car and hiked in the snow to a place that opened up some views.
The “problem” was: I had two options – a nice view to the south and a nice view to the west of me. Being photo-greedy I decided that I would first shoot the south vista and then the west one. However, during sunrise and sunset, the best light can last only for a couple of minutes. Despite the fact that I was well aware of that, I decided to take the risk and attempt both images.
I set up for the south view and began waiting. The light started changing, but it wasn’t great, so I kept shooting and waiting. I got so distracted that I completely missed some of the most amazing colors in the sky to my right – the west view. Essentially, I was chasing a less attractive option while magic was happening to my side without my noticing it.
Scrambling, I moved my camera and repositioned in an attempt to capture the west view. Because of the snow and my hurry, I had a hard time setting up the camera, and it took me much longer than it normally takes. By the time I started shooting the best light was gone. I captured the tail end of it. In my hurry however, my lens focus was not dialed in, resulting in blurry images.
The end result of that entire effort:
– I didn’t get enough sleep that night
– I lost hours in driving
– I could not really enjoy the sunrise
– I came home with zero good images
I tried to sit on 2 chairs at the same time and ended up on the floor.
You want to be ambitious in your goals but at some point a line is crossed where greediness blinds us to reality and we end up with nothing. It is better to maintain focus and go after the most important thing first. If time and ability allow for more, more can be pursued then.