Implementing Project Management Software

My team and I once tried to hand-wave our way past Jeff Bezos with a large headcount request. He asked one question, was disappointed by the answer, and dug deeper. After a weak answer to question two, it was game over. Jeff declared that he trusted NONE of our proposal and sent us back, telling us, "Break down your requests to no more than 2 or 3 heads, tops, per line item. Then explain exactly what these small buckets will do." Once we did this, he went through the request line by line, telling us what we could and could not have. Overall, it was probably the most brutal experience I had with him in my 15 years at Amazon. While some people will read this and feel it was micromanagement, he was entirely right. We thought we had a blank check, so we made a big, broad funding request. We learned very quickly that while Jeff supported our mission, he expected us to spend "his" money carefully. Most people think executive influence happens in the room, by talking slick or having the right alliances. While communication and connections are hugely important, most of your influence is built before the meeting starts. Getting executive buy-in comes from understanding your executives, anticipating their concerns, and structuring your message around what they value. Here are two quick specifics: 1. Preparation If you walk into a key stakeholder meeting without preparing, like I did, you’ve already lost. The first step in preparation is clarity: What are you trying to achieve, by when, and why now? Then, define exactly what you’re asking for: a decision, resources, or permission to move forward. Finally, decode the humans. What does each stakeholder care about? What do they fear? How do they make decisions? Build your case in their language and plan your approach with intention. 2. Focus on Facts Executives are moved by accurate, outcome-driven facts. Shortly after this disastrous headcount audit, I was asked to lead the global expansion of the Kindle Appstore. This required taking 55 engineers away from other executive leaders to staff our rush effort. Our team won support by anchoring on three facts: (1) Kindle’s success in the U.S. was undeniable (2) The holiday deadline couldn’t move (3) Leadership had already approved a one-year draft to make it happen. Those facts aligned perfectly with what executives valued most: growth, timing, and company priority. If you master these skills, you’ll earn trust and support from senior leaders. In large organizations, this translates to success in your projects and success in your career. I've written a much more in depth Newsletter that covers these skills and more: https://lnkd.in/geEBPazP When have you either fallen into hand-waving or had to call your team on it?

I’ve now been involved in buying software at 4 companies. I never realized how many mistakes I was making as an AE until I was on the other side. Why is “How we buy” not a part of every AEs onboarding? AEs listen up. Here is where I got it wrong and what I think is important to understand: 1️⃣ Your buyer has a full-time job. Evaluating software is an additional task that is time consuming, requires some internal political pull and can likely mean they are putting themselves (or their jobs) on the line. Understand this and don’t take it lightly. It’s important you understand whether this person has bought software before and HOW RECENTLY. Why? If I happened to just buy a software last month, I likely used up some of my “internal pull” and energy on it. This matters more than you think. 2️⃣ Buying cycles are slightly different based on whether somebody came inbound or outbound. If I request a demo, it may be out of curiosity, but usually this is an initiative that has already been talked about internally with various stakeholders, potentially a budgeted line item and half the decision has already been made. This person is likely a champion, needs less convincing of the problem/solution and is probably talking with other vendors. Focus on differentiation early here. For outbound, this potentially means a much larger uphill battle for your buyer. You must identify key stakeholders early and start multi-threading and helping that champion sell. One of my favorite things to do here is spin up a digital sales room like Aligned and uncover who is actually looking at the material I’ve sent over. 3️⃣ Buying software is not rooted in rationality. Humans are not rational actors. Your ROI numbers are likely irrelevant… especially if we didn’t specifically sit down and confirm them. Example: Let’s say your solution ultimately helps me get more qualified pipeline. There are HUNDREDS of ways that I can go about doing this. Better contact data, better signals, better research on accounts, better emails, better training etc. You need to help me prove that you are the BEST way to do that. 4️⃣ Make it extremely easy for me to sell internally. No exec watches demo recordings, reads case studies or has time for 20 slides in a deck. Gal Aga said it best in a post the other day: 1. Equip them with a CXO-ready business case 2. Co-build all internal assets (ROI, TCO, FAQs) 3. Pre-plan rollout (beyond just closing) 4. Pressure-test expected internal objections 5. Prep champions for CFO skepticism 6. Map risks openly—no deal is risk-free 7. Constantly challenge: "What could kill this project?" Please don’t just send over a bunch of links or PDFs. Get yourself Aligned and make it easy for buyers to have a hub with all documentation in one place. Try it for free here: https://lnkd.in/eqcE6G9r

We just closed a $480K deal at Aligned - our biggest ever. But twice in the final weeks, it almost died. It was brutal. Two execs came out of nowhere with objections. We had no access. No time to fix it. But 22 (!!) stakeholders had already been engaged… And they saved it. That’s when it hit me: Multithreading isn’t a tactic. It’s deal insurance. Here’s the exact playbook we now run in every complex deal: 1. Early Exec-to-Exec Sponsorship Don’t wait until sh*t hits the fan. Initiate VP-VP or CXO-CXO alignment early. We send short, supportive emails without direct asks. Time after time, that builds genuine trust and establishes a safety net long before we need it. 2. Identify ‘Hidden Stakeholders’ Buyers often silently forward materials internally. By using Deal Rooms, we uncover up to 68% more stakeholders, often the real decision-makers influencing budget approvals or strategic buy-in. 3. Isolate Stakeholders 11 people on a call? You’re NOT multithreaded - it’s about quality, not volume. Our team opens separate 1:1 convos. They follow up with each buyer with next steps, suggestions or value that ties to something they said. 4. Proactive Signal-Based Engagement When stakeholders interact with key assets in the deal room, we use those signals to trigger follow ups - e.g. RevOps spends 20min on CRM integration; they might need more info, or could benefit from a dedicated session. 5. Multiple Champions Strategy Nothing beats having an army of internal champions instead of one. Whenever we see an opportunity to build champions, we do it. It derisks the deal in case someone leaves. Plus, budgets are shared, or are just easier to pass. 6. Real-time Alerts on New Stakeholders Our deal room sends instant alerts whenever there’s a new stakeholder (see #2). We then leverage this event as an opportunity for exec introductions or quick alignment note—”Hey, saw you joined the project”. 7. Support the Above-the-Line (ATL) Met an exec early? Keep them looped into POC updates, key milestones, or call takeaways. When we give regular status updates, it builds credibility and keeps momentum - as execs don't join every call, and appreciate the visibility. 8. Never Underestimate Below-the-Line (BTL) Decision-making today is flatter; end-users/junior stakeholders are increasingly influential. I’ve lost count on how many times AEs (our BTL buyers) were make or break in our deals. Give them genuine attention. Don’t underestimate any buyer. 9. Late-Stage Exec Reinforcement If a deal stalls, a concise, confident, personal email from me as CEO resets urgency. The message isn't pushy; it reinforces our shared vision, driving commitment. —— Multithreading isn’t a tactic. It’s insurance. A deal defense system. Built thread by thread, stakeholder by stakeholder. So when things break, and they will - You’re not the only one left to save it. P.S. The Deal Room we used to multithread is Aligned. It's free to try: https://lnkd.in/dYksGnfb

Tactic 2 for influencing stakeholders from Jules Walter: Frame your message from their POV (not yours) It’s more effective to speak their language and demonstrate how your proposal will help them reach their goals, not yours. Stakeholders are focused on their own problems and are more receptive to proposals that address what’s already top of mind for them. A few years ago, when I was leading Monetization at Slack, we began to encounter diminishing returns in our product iterations, and we needed to take a bigger swing to re-ignite revenue growth. To do that, I spearheaded a controversial project to experiment with a new approach to free-to-paid conversion. The CEO, Stewart Butterfield, had strong reservations about the project. I knew from his previous statements that he didn’t want the company to be thinking about ways to extract value from users, but rather ways to create value for them. We had scheduled a review with the CEO and a few of his VPs to discuss the proposal. Since he was intensely user-driven, I framed the entire proposal around the benefits it would have for users (the CEO’s POV) rather than emphasizing the revenue impact of the project (our team’s goal). I started the meeting by anchoring the proposal on user-centric insights that we shared in a deck: - “About 10% of purchases of Slack’s paid version happen from users in their first day on Slack.” - “Paid users find more value and retain better. Yet we make it hard for people to discover that Slack has a paid version that’s more helpful.” - “How do we help new teams experience the full version of Slack from the start?” Once we framed the issue with this user-centric lens, the CEO was more open to our proposal and let us try a couple of experiments in this new direction. This user-centric framing also got the cross-functional team more excited and set an aspirational North Star with clear guardrails, which then enabled various teammates to contribute productively to the project. After we tested two iterations of our monetization experiment, we landed on a version that resulted in a significant increase in revenue for Slack (a 20% increase in teams paying for Slack) and we used what we learned to shift Slack’s monetization strategy into a new, more successful direction. Full set of tactics here: https://lnkd.in/gezP2EDw

Ever presented rock-solid research only to hear "Thanks, but we're going with our gut on this one"? Securing stakeholder buy-in is rarely about the quality of your work. It's about something deeper. When you’re dealing with a research trust gap, ask yourself 5 questions. 👽 Are you speaking alien to earthlings? When you say jargon like "double diamond" or "information architecture," your stakeholders hear gibberish. Business leaders didn't learn UX in business school—and most never will. Translate everything into business outcomes they understand. Revenue growth. Customer retention. Cost savings. Competitive advantage.  Speak their native language, not yours. ⏰ What keeps them awake at 3am? Behind every skeptical question is a personal fear. That product manager who keeps shooting down your findings? They're terrified of missing their KPIs and losing their bonus. Have honest conversations about what they're personally on the hook for delivering. Then show how your research helps them achieve exactly that. ❓Are you treating assumptions as facts? You might think you know what questions matter to your stakeholders. You're probably wrong. Before starting research, explicitly ask: "What questions do you need answered to make this decision?" Then design your research to answer exactly those questions. ⚒️ Are you dying on the hill of methodological purity? Sometimes you have 8 hours for research instead of 8 weeks. Being dogmatic about "proper" research methods doesn’t always pay off. Focus on outcomes over process. If quick-and-dirty gets reliable insights that drive decisions, embrace it. 🍽️ Are you force-feeding them a seven-course meal when they wanted a snack? Executives need 30-second summaries. Product managers need actionable findings. Junior team members need hands-on learning. Tailor your approach to each one. You can also use my stakeholder persona mapping template here: https://bit.ly/43R7wom What’s the best advice you’ve heard about dealing with skeptical stakeholders?

Want buy-in from business leaders? Stop using technical language. This is probably the lesson that took me longest to learn and it's the one that's made the biggest difference in my career. Early on, I would walk into meetings with CMOs, CFOs, and COOs and start talking about semantic layers, data orchestration, observability, and pipeline architecture. Their eyes would glaze over. And then they'd deprioritize my projects. It wasn't because the work wasn't valuable. It was because I was speaking a language they didn't understand and honestly, didn't care to learn. Now I do it completely differently. When I talk to a CMO, I use their language. I talk about customer acquisition cost, consumer lifetime value, and CRM performance. I reference the metrics from their last board presentation. I say things like: "That report that takes you 14 weeks to get? Here's how we fix it so you get it in 4." That lands. That gets attention. That builds trust. I spend the first four to five months of any new role just building relationships. One-on-ones with as many stakeholders as possible. Learning their pain points. Understanding what success looks like for them. I'm not coming in to fix things right away. I'm coming in to listen. Because here's what I've learned: People don't do business with you because you have the greatest tool or the smartest team or the most impressive architecture. They do business with you because they like you. They trust you. And they believe you actually care about solving their problems. Relationships > Tools. Every single time. Once you have the relationship, the technical stuff becomes so much easier to execute. Doors open. Resources get allocated. Priorities shift in your favor. But without that trust? You're just another cost center asking for budget. How do you build relationships with non-technical stakeholders? 👇 #Leadership #Communication #ExecutivePresence #DataLeadership #Influence #Stakeholders

You've chosen the AI tool. You've rolled out the policy. You've told everyone to use it. Why isn't anyone using it? What tends to happen usually in AI adoption is a top-down implementation: • Management selects an AI solution (often without user input) • They announce the new tool with fanfare • They roll out a policy document • They say: "We can use it now" • Then they wait for results Three months later, adoption is minimal.  The AI sits unused.  The project is labeled a failure. The missing piece? Effective change management. Change management isn't about glossy slide decks or mandatory training sessions. It's about bringing humans along on the journey. It looks like: • Consulting users at every step of the journey • Involving key stakeholders in tool selection • Creating AI champions within teams who can demo products • Establishing two-way feedback channels • Testing workflows with the people who'll actually use them You need to balance 2 critical communications: 1. Benefits: "This could genuinely make your work easier. Let's collaborate to get the most from it." 2. Risks: "I need your help watching for potential issues so we can address them together." When people feel a sense of agency and ownership, they become invested in the project's success. When they feel like cogs being forced to adapt to a new machine, they resist. You see, success isn't determined by the technology you choose, but by how well you bring your people along. The AI tool might be management's decision, but adoption is each individual's choice. Make them partners in the process.

🙋♀️ How to Introduce Change in an Organization Facilitating transformation is a key literacy for healthcare leaders. In my role opening the new Texas Children's Hospital Austin over the past 3.5 years I worked with lots of young docs who wanted to start things — Programs, tech projects, unique service lines. I was their first stop. But creating something de novo in the largest pediatric healthcare system in the country takes an intentional approach. It doesn't work like a startup. This is what I told them 👇👇👇 1️⃣ Define the change You need a clear vision. 👁️ I do this with a 1-2 page executive summary. Something pithy, subdivided, visionary with clearly thought out operational steps. This should be developed (in your head) with a compelling elevator pitch for those critical hallway conversations. Remember that your vision summary is as much for you as it is for anyone else. You'll never know what you're thinking until you write it down. I never see the subtle lapses in my logic until I've put it on paper. 2️⃣ Create the value proposition Spell out why the organization needs your initiative. 🔡 Anchor your vision in something real: inefficiency, burnout, lost revenue, patient harm, missed opportunity. And be ready with clear benefits. This is where you help skeptical stakeholders visualize how good this will be to the organization. If you can create a sense of urgency it will help your cause. 3️⃣ Seek alignment Get key folks on board. One by one. 🚣♀️ I then disseminate this concept sheet to the highest practical level of leadership in the area want to change — in my case an senior or executive VP. This is key: I share this strategically with one person. The sense of selectivity that comes with knowing they were my first stop can be powerful . With buy-in from someone of influence, I then leverage this on my next stakeholder pitch to players who are more likely to help me bring this thing to reality. 4️⃣ Create proof of concept Show people what you got. 🎭 When you're selling something there's nothing better than evidence — the thing that helps people see the reward for participation. A living example; a brief trial, pilot, etc. In my organization you sometimes just have to bootstrap it and start in order to get to that first tangible chunk of success. 👉 Remember the bigger the organization the more likely you'll meet resistance. It's like gravity, only more annoying — You have to accept it and deal with it. Don't take it personally. Understand that pushback will come and counter with that clear, solid value argument. Persistence, consistency, and time are key elements in getting there — that can be the hardest part. 🐶 Eating the dog food — I just started a bold project of my own and had to use these steps. And every time I do this I learn something new. How do you start something? 📰 If you like this, check out my newsletter https://lnkd.in/g5GWsep3 #Leadership #Hospitals #Healthcare  #management

"My product is internal only. My user base is captive - leaders will force them to use." Ring a bell - many PMs building internal products think this way. "I build products based on requirements given by 1 business stakeholder - s/he will ensure adoption. I build, adoption is not my headache." If you are in this boat, time to wake up. Think like a real product manager, not a project manager. Here's how you can behave and showcase your true PM skills, by caring about meaningful product adoption: 🔍 Understand Your Internal Users: Treat your colleagues as customers. Conduct user interviews, surveys, and usability tests to understand their pain points, needs and workflows. Just like external customers, internal users have unique requirements and expectations. 🛠 Iterate Based on Feedback: Gather continuous feedback from users. Use this data to iterate and improve your internal product, ensuring it truly meets the needs of your users. 📈 Drive Adoption: Adoption is the internal product’s equivalent of growth. High adoption rates indicate that your product is valuable, user-friendly, and effectively solving problems. Monitor usage metrics, engagement levels, and satisfaction scores to gauge success. 🚀 Champion Internal Advocacy: Encourage your teams to pitch your product on any stage available. Create compelling training materials, host workshops, and provide excellent support to make it easy for users to adopt and champion your product. 🔄 Align with Business Goals: Ensure your internal product aligns with broader business goals. Demonstrating how your product contributes to overall efficiency, cost savings or any other objective and key result committed by your team. If you really think about it, you can erase the boundaries between an internal or external product. A product is a product, period. And your role as a product manager for an internal product is as critical as a PM for an external profit-making product. If you are not continuously obsessing about product adoption, you are not really doing your core work - you end up being a project manager or an engineer at best. #ProductManagement #InternalProducts #UserAdoption #ProductDiscovery #GrowthMindset #OrganizationalSuccess

A designer once told me, “This is amazing…but I already committed to a solution.” That’s when it clicked: Research doesn’t drive change. Alignment does. The best researchers I’ve worked with? They’re not just insightful. They’re influential. Here are 6 habits of researchers who consistently get buy-in and how to start using them today: 1. They never say “users were confused” They say: “This issue is costing us 12% of conversions.” ↳ Take one insight you’ve already shared and rewrite it using this format: Problem + Impact + Recommendation Then send it to one stakeholder as a Slack message, not a deck. 2. They don’t deliver research. They facilitate decisions They ask: “What’s the decision this team is stuck on right now?” ↳ Before every project kickoff, ask your PM: “What’s the riskiest assumption behind this decision?” Then shape your study around that. 3. They translate like hell Not “delight,” but “adoption.” Not “friction,” but “drop-off.” ↳ Pick 3 insights from your last study and rewrite them using business terms. Drop them into a meeting and watch who starts paying more attention. 4. They time it perfectly Not a 30-slide deck on a Friday. A one-sentence quote right before a roadmap review. ↳ Look ahead to next week’s big decision-making moment. Pick one insight and share it 24 hours before the meeting. Not during. Not after. 5. They repeat themselves intentionally They plant insights until someone else says it back to them. ↳ Pick one finding you want to stick. Mention it once in Slack, once in a retro, and once in a 1:1 this week. Different formats. Same message. Let it echo. 6. They stop trying to “educate stakeholders” They listen. They co-create. They shift the power dynamic. ↳ Instead of sending research after it’s done, invite a stakeholder to help design one question before it starts. You’ll double your buy-in before you even begin. You don’t need stakeholders to love research. You just need them to feel what it protects them from. If your insights are strong but your impact is quiet, making these into habits is your next step. Which of these habits are you building right now? Or what’s one you’d add to the list?