Assessing a New Career Opportunity for Its Potential

Experts share their advice on assessing an organization's readiness for change from the outside

At some point in their career, every leader evaluates their current role and wonders—is it time to look for something new? Would a different opportunity accelerate their career? And the biggest question of all: “would I be able to make a real impact at another organization?” 

All too often, organizations claim to be committed to working in a new way and driving change forward, only for new hires to quickly realize the reality is much different. We spoke to four change leaders to learn what they’re found most helpful in determining what to look for when considering a career move: Katy Jordan, SVP of Digital Marketing, TrueSense Marketing; Caroline Raj, Senior Director and Head of Marketing of Australia and New Zealand at ServiceNow; Alex Scriven, COO, Adatree; and Steven Stanton, Executive Director Investments, First Australian Capital.

As you evaluate potential opportunities, they suggest keeping the following in mind:

Before Interviews

Look for a proactive organization. If an organization approaches you directly, it isn’t just flattering, it shows “that they’re looking for a skill set to come in and create the change,” according to Stanton. Are they looking for a transformational leader, rather than an accountant? Do they know who they want as a leader to lead the change piece? Is it too early for me as a leader?”

During Initial Interviews

Identify your assumptions about the role, and test them during your interviews. The role description serves as an excellent starting point for determining what you, and the organization, expect to achieve during your tenure, so use early interviews to assess whether you’re on the same page. Or, as Raj phrases it, ask “What are the three things that I can do to meet your expectations, and what are three things I can do to delight you?” These questions will quickly help you determine if your expectations are misaligned with the organization’s. Of course, when discussing potential future goals and plans for change, tone is important. “The biggest risk of this approach is being perceived as a know-all,” notes Scriven. “Have an idea of where things could go, and ask the relevant questions, but don’t tell the executives what to do.”

Dig into prior examples of changes within the organization. Ask questions about how the organization has supported change leaders in the past, and what that support could look like for your role. “Ask about the projects and specifics: who’s worked on the project? Who was the owner who funded it? Have they actually delivered that?” says Raj. Jordan encourages candidates to ask potentially uncomfortable—but relevant questions—“How have you navigated a conflict when you’ve got two business leaders in discord? Or, your executive team developed a strategic plan without team input; how did that go over with the team?” According to Scriven, “In the right organization, these questions would be regarded as a positive: this person is thinking about actually affecting change, and not just making up the numbers.”

Check for internal leadership alignment and enthusiasm for the change. “Can the hiring party consistently articulate what they’re trying to achieve? Is the vision clear?” asks Stanton. If you’re not getting a consistent message about the strategic direction of the change, your role may ultimately be in jeopardy. “I was in the room with the executive responsible for delivering a vision, and asked her, what really excites you about this new line of business?” Scriven shares. “And she couldn’t answer the question because it was clear that she wasn’t excited at all… The company shut the program down only three months later.”

Test for leadership style. “The style of leadership to me is a really important part—I’m a big believer in being around people who energize you,” says Scriven. Arguably, ensuring your leadership style meshes with others is the most important factor: “It’s maybe 20% skill set, 40% interpersonal skills and who you are as a person and your core values; and 40% leadership; your ability to create leadership internally. I look for more focus on attracting leaders, rather than the hard skills,” notes Stanton. At the same time, be careful about making your decision solely based on current leaders. As Raj cautions, “You never know how long those leaders and managers will be in the role. You have to decide whether it’s an organizational culture fit, not just a manager fit.”

Assess how they communicate, not just what they communicate. The hiring process itself can give you important clues about how the organization conducts business, and how committed it is to change. Stanton warns, “Watch out for someone who flip flops between engagement and disengagement: you’re a priority, then not a priority. Strong onboarding, and then things go quiet. When you’re ready to sign, suddenly they’re not transparent.” The organization’s structure and leadership can also indicate its true priorities. For instance, Raj looks at the organization’s diversity: “If you’ve got a board or executive leadership that’s all men, you have to question whether they really do internally want to change.” Stanton, meanwhile, noted that churn rates at lower levels of the organization can be an early indicator of potential problems.

Additional Interviews and Independent Research

Meet with representatives from different levels within the organization. To get a more comprehensive view of the organization, ask to meet with individuals representing different levels of the hierarchy, ideally in a more casual setting. Stanton recommends inviting other members of the leadership team out to dinner to “get their views while the CEO is out of the room,” while Raj suggests a coffee chat with “someone who’s a little bit lower down—they can actually tell you about the culture a bit more, and they won’t filter as much.”

Be critical of online reviews. “You can certainly google, look at Glassdoor, but these days, those things are also easy to make it look good,” says Raj. That said, there may be some limited benefit to doing online research: “If there’s consistent feedback—if employees have been complaining about the same thing five years ago and six months ago—that’s an indication that progress isn’t being made,” notes Jordan.

Explore targeted topics with your network. The most consistent recommendation was to use your network to determine the accuracy of the information you’re hearing during the interview process. You don’t necessarily have to find people within the organization itself; suppliers, vendors, and other partners can be critical sources of information. Raj suggested finding one or two people who know the organization and being very specific about the questions you ask. Similarly, Scriven suggested using these individuals to validate what you hear in interviews, and then “crafting your questions back to the people in the interview in different ways.” That said, everyone stressed the importance of sensitivity: don’t put your network in the position of breaching confidentiality.

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