Overcoming Trust Issues in Software Development Deals

“WebSphere was a bazooka designed to kill an ant and Tivoli was Latin for boat anchor”. These are two real cliché examples how the software industry feels when they have been oversold and underdelivered which they have for the last 25 years.  There are many more including several in today’s software packages and providers including cloud and SaaS. Therefor if you are new and engaging with one of these customers who have had poor experiences you’re not trusted, and they have not even met you yet? Wait what? So, I am being judged by my predecessor ? Yep, you are and here is how to change that: 1. Brutal honesty. I was notorious meeting new CIOs with sales reps  and opening with “ if my rep tells you it is out of the box functionality I will throw them out of a 25 story window” CIO smile… why because he knew that his environment was key for any success and we established upfront we were different and they have been through the “out of the box” pitch before and suffered. 2. Self-deprecating humor.  Have the courage to bring up the past.  If your company has made some mistakes bring them up first. I was clear at CA that Unicenter the framework looked great on a whiteboard but later we found that making it more modular and integrated where only necessary was a better approach. C level "hmm ok that makes sense”. I also used to tell CIO’s I was doing the Oprah apology tour around NA and then asking to be judged on my results moving forward ….it worked.  BMC same I loved looking for and talking about the death star diagram … people said well it didn’t quite work and my response was none of this turns out perfectly lets talk about why and what we learned from  it … customer response “ OH that makes sense. “ 3. Be a doctor. Ask way more questions. “Can I help you ? I don’t t know; I need more information. Some people take a Z pack for everything not me I want a doctor to look for symptoms. Let your prospect know you will not sell them anything without getting the information to determine if they are sick.  Make it clear you will move on if you can’t really help them.  * courage is mandatory #trustbuilding #honesty #integrity #doctor #valueselling #lifelongconnections

This morning, we were ready to deliver our client’s content folder at ORA Marketing, but things didn’t go as planned. Twice now, we’ve faced the same challenge: right before delivering our final product, we discovered a glitch in the audio recording. After some digging, we realized it wasn’t an error from our team or the client—it was a glitch in the software we use. And as a team that takes immense pride in delivering high-quality content and delivering on time, this hit hard. When you’re aiming to exceed client expectations, and this happens twice in a row, it definitely takes the wind out of your sails. It’s frustrating, but it’s also part of the job: things go wrong, and your response matters more than the setback. Two big lessons came out of this experience: 1. Communicate Proactively & Take Ownership We reached out to our client immediately, taking responsibility not just for what we could control but also for the software issues out of our hands. This approach—owning the full experience—made a huge difference, and our client’s response was amazing. They appreciated the transparency, and it deepened our trust. 2. Partner with the Right Clients It’s easy to work with clients who see value in the partnership, even when things go wrong. In this case, our client could have walked away, but they stuck with us because of the solid relationship we’ve built. When you’re aligned with your clients, you work through challenges together, finding solutions that benefit everyone. If you’ve ever been in a similar situation, remember: communicate openly, take ownership, and—before it even gets to that point—make sure you’re working with clients who value the partnership as much as you do. It makes all the difference.

Most software development firms avoid talking about cost estimates early on. I think that’s a mistake. When a client asks, ‘How much will this project cost?’ too many companies beat around the bush: ’We need to do a full requirements analysis first...’ ’There are too many unknowns right now...’ I get it. I used to do the same. But here’s the truth: nobody wins this way. The client loses trust, and might walk away. The firm wastes time not knowing if the project is even a fit. Here’s how we do things differently at Wozify and Astro42 - A Wozify company: After a 30-minute conversation, equipped with years of experience, I always give a ballpark estimate. Something like: ’Based on similar projects, this would likely fall between 50k and 100k. Does this align with your expectations and budget?’ Or if the details are still unclear: ’There are a lot of unknowns, but in our experience this would start around 150k, and could go much higher if there’s lots of R&D involved.’ I make it clear this isn’t a binding quote. We still need detailed discovery to define the value proposition and flesh out the requirements. But at least now, everyone’s on the same page. Some negotiation experts might say I’m shooting myself in the foot. But this approach saves everyone time, especially if our ballpark estimate is way off from what the client had in mind. It also builds trust, right from the start. Being upfront about cost estimates isn’t just honest. It’s efficient, and it’s respectful to both sides.

Despite the importance of delegation within an organization, I still enjoy taking sales calls with prospective clients. It’s fun to meet new people with ambitious ideas and learn about their products. However, not every call is filled with excitement and opportunity. Sometimes, I hear horror stories that would rival a Stephen King novel. These stories often come from clients who have had bad experiences with other agencies. Whether it’s being ghosted mid-project, receiving sub-par work, or being misled by false promises, these tales are all too common. One of the most frequent issues I encounter is agencies failing to provide comprehensive documentation at the end of a project. This oversight can be detrimental, leaving clients struggling to maintain or scale their products effectively. Documentation isn’t just a formality; it’s a roadmap for the future, ensuring the client can navigate the intricacies of their software without constantly relying on the original developers. But the most terrifying scenario I’ve come across is when agencies hold a client’s source code hostage. Some companies forget that as a software development agency, you’re providing a service for hire. Just because you built it doesn’t mean you own it. This can lead to a nightmare for the client, who is left without access to the very product they paid to have developed. To avoid these pitfalls, it’s crucial for clients to discuss these matters upfront and ensure their contracts are well-written to protect their intellectual property. As a client, always make sure that all source code and documentation are stored in accounts registered under your name. It’s a small step that can save a lot of trouble down the road. In the end, the key takeaway is simple: transparency, communication, and proper planning are essential for a successful partnership. And despite the challenges, being a part of these conversations and helping clients navigate these issues is why I still love taking those sales calls.

With more than a decade in the business, I’ve learned that one method always helps me seal high-end deals: BE TRUTHFUL. It may sound simple, but being genuine and transparent is incredibly powerful in building long-lasting relationships and trust with clients. I remember a particular deal a few years back. We were in the final stages of negotiation, and I knew that our solution wasn't a perfect fit for one aspect of the client's needs. Instead of glossing over it, I openly discussed the limitations and how we could work together to overcome them! 🤝 To my surprise, this honesty strengthened our rapport. The client appreciated our transparency and chose to work with us, not just because of our capabilities but because they trusted us. That deal turned into a long-term partnership, leading to more opportunities and mutual growth! 😀 We have to understand that none of us is perfect, and there is strength in acknowledging that! ✨ Being truthful doesn't mean exposing every flaw but rather maintaining integrity in our communications and actions. What’s your go-to method for building trust in deals? #businesslessons #softwaredevelopers #appdevelopers #techfounders #startups #techstartups #businessleaders