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Considerations on That Startup Life

In 2008, I was working for a major telecom company, handling calls for large business and government accounts. One day, while looking at an organizational chart, I realized my only available career moves within the company were lateral. I could shift to data support or something similar, but there was no clear path upward. I needed to move on. I searched online but couldn’t find many customer service options in New Jersey, where I lived. Then one night, it dawned on me to check New York. Believe it or not, I found my first job at a startup through Craigslist. Here, I'll share some of my thoughts on startup life. First, in a startup, you wear many hats. I was hired to provide "white glove" service to our clients, but with only a handful of customers, my primary role became content preparation. I processed investment newsletters from print, email, and PDFs into a format that our web application could display. Along the way, I also took on minor technical tasks, like fixing ...

The Value of Workplace Curiosity

Many people approach work with a "clock in, clock out" mindset. While this might get the job done, it limits personal and professional growth. You may become highly proficient in your current role, but what you truly need is experience that prepares you for the next one. Developing curiosity about different roles can expand your skill set and open new career opportunities. Exploring other roles broadens your understanding of the organization. Observing how different teams and departments function helps you see the bigger picture, while understanding cross-functional collaboration improves teamwork and efficiency. This, in turn, enhances your own job performance. Exposure to different roles provides valuable insights that can strengthen your current work, offering fresh perspectives and problem-solving strategies. Ultimately, this creates career growth opportunities—having a diverse skill set makes you more adaptable to change, and familiarity with adjacent roles increases you...

Redefining My Calling: Ministry, Career Shifts, and Finding Purpose

In my late teens and early twenties, my sole career focus was ministry. When I first expressed this calling, I quickly realized that traditional congregational ministry didn’t feel like the right fit for me. Seeking guidance, I approached the pastor of my church—part of the Presbyterian Church (USA) —to ask if there were alternative paths in ministry. Unfortunately, he didn’t have the time to discuss it, and before we could follow up, I had moved on to college. In college, I continued preparing for ministry, but every discussion and lesson centered on congregational work. Over time, I became so immersed in that narrative that I lost sight of any other possibilities. After a brief yet relatively successful stint as a missionary in Brazil, I accepted a call to serve a small church in New Mexico, part of the Christian Churches/Churches of Christ . It turned out to be a terrible experience. One elder regularly solicited critiques of my work from the congregation and then relayed them to me...

What to Do When You Aren't Laid Off

Being laid off is terrible. Having been laid off a few times myself, I know well the shock and anxiety of the experience. This post isn't about the people who are laid off, though. It's about those left to carry on. What follows is my advice to survivors of layoffs. First, take time to process what's happened. This is often said to people being laid off, but it's not much use to them, as generally they have no time to waste in this job market to look for another job.   For someone who has made it through a layoff there can be a variety of feelings. Acknowledge your emotions, whether it's relief, guilt, anxiety, or sadness. It's normal to feel a mix of things. Second, support your former colleagues. Reach out to those who were laid off, particularly via LinkedIn. Offer emotional support, job referrals, or networking help if you can. Even better, check in on them a month or two later for these things. People when laid off often have a flurry of activity in the beg...

Managing Ambiguity When Requirements Are Unclear

One of the most challenging aspects of project and program management is dealing with unclear or constantly evolving requirements. Whether due to shifting business priorities, incomplete stakeholder alignment, or rapidly changing market conditions, ambiguity is an inevitable part of managing complex initiatives. Your ability to navigate this uncertainty while keeping the project moving forward is what sets you apart as an effective leader. Here’s how you can manage ambiguity and bring structure to chaos. First, clarify the big picture. When requirements are vague, step back and focus on the broader business objectives rather than getting lost in missing details. Ask stakeholders: What problem are we solving? What does success look like? What are the key constraints (timeline, budget, resources)? Aligning on these high-level priorities ensures that even if the details shift, you have a north star guiding the project. Second, break down unclear requirements into known and unknown compone...

The Kick-Off Meeting: Follow Up

Following a project kickoff meeting, the real work begins. While a well-run kickoff sets the stage for success, what happens immediately after the meeting is just as important. Without proper follow-up, even the most productive discussions can lose momentum, and critical action items may slip through the cracks. Ensuring a smooth transition from planning to execution requires timely communication, clear documentation, and alignment on next steps. The first and most immediate task is to send out meeting notes. These notes should capture key decisions made during the kickoff, major discussion points, and most importantly, action items assigned to specific individuals. A well-structured summary not only reinforces what was agreed upon but also serves as a reference document for those who may have missed the meeting or need to revisit details later. Meeting notes should be concise but comprehensive enough to provide clarity on responsibilities, deadlines, and any unresolved questions. Dis...

The Kick-Off Meeting: Execution

In a previous post, I covered how to prepare for a project kickoff meeting. Now, I’ll discuss a solid format for running the meeting effectively. As I noted before, my early kickoff meetings were fairly informal—I would gather the right people, let them talk it out, and capture action items. While that approach had its merits, it wasn’t structured enough to ensure a project got off to the best possible start. A well-run kickoff meeting should set clear expectations, align stakeholders, and establish a foundation for success. The meeting should begin with a welcome and introductions. As the project manager, you are the host, and your role is to set the tone and facilitate a productive discussion. Introductions help build rapport among team members, especially if they haven’t worked together before. Having each participant share their name and role in the project is a good start, but adding an icebreaker can make the meeting feel more engaging. Something simple like “one thing people do...

The Kick-off Meeting: Preparation

Early in my career, as I transitioned from site producer to associate project manager, I didn’t have much formal guidance on how to do my job. Instead, I relied on observing experienced project managers and learning from their examples. Over the years, I’ve honed my skills in managing dependencies, facilitating discussions, and simply running effective meetings—essential skills for any project manager. One of the most critical meetings in any project is the kickoff meeting. It sets the stage, aligns stakeholders, and ensures everyone is working toward the same objectives. This post is the first in a three-part series on kickoff meetings, beginning with preparation, followed by execution, and concluding with follow-up. The first step in preparing for a successful kickoff meeting is creating a solid agenda. Early in my career, my approach was fairly loose—gather key stakeholders and the project team, present the scope, let them discuss, and then take follow-ups. While this method works, ...

Effective Vendor Management: Lessons from Experience

In several of my roles as a project and program manager, vendor management has been a key responsibility. In one role, I managed vendor relations for a proof of concept (POC) to determine the best technology solution for a core business process. In another, vendor management was a significant part of my day-to-day work. Based on these experiences, I’ve learned that successful vendor management requires clarity, streamlined communication, and robust tracking. Here are three essential strategies for managing vendor relationships effectively. 1. Establish Clear Expectations from the Start One of the most critical aspects of vendor management is setting clear expectations from day one. This includes: Defining scope, deliverables, timelines, and quality standards upfront. Establishing clear Service Level Agreements (SLAs) and Key Performance Indicators (KPIs). Ensuring vendors fully understand project priorities and dependencies. A key lesson I learned in one of my roles involved receiving ...