Managing Your Boss: The Key to Success within the Digital Travel Sector

To many people, the phrase "managing your boss" may sound political, even cringeworthy. However, we can all agree your relationship with your boss is crucial to achieving the best possible results for you, and the company. You rely on them for support and opportunities, and they need your cooperation, reliability, and honesty to achieve shared goals. A poor relationship with your boss can lead to missed opportunities, decreased job satisfaction, and a negative impact on your overall well-being and company performance. As the saying goes, “A boss who doesn't trust you won't offer opportunities, and a company that doesn't see value in a team will have no choice but to pivot quickly.” Therefore, it's essential to establish an interdependent, collaborative relationship with your boss to pave the path for mutual and company success.

Throughout my career, I've predominantly worked in fast-paced TravelTech companies. On one occasion, I worked on a major project that required close collaboration with several technology and commercial teams across multiple countries within the Asia Pacific region. My boss, who was overseeing the project, emphasised the importance of adhering strictly to the Asia Pacific regional direction he had outlined.

I, on the other hand, saw an opportunity to tailor our approach to better suit the Australian local market. I closely coordinated with the Australian-based teams, assuming advocating for the Australian traveller’s needs would naturally align with the overall project strategy. Nevertheless, I failed to clearly communicate these deviations to my boss.

As the project progressed, these deviations began to surface. During a critical review meeting, it became evident that our Australian modifications conflicted with the overall project strategy. The lack of alignment between my boss and me caused delays and confusion among the broader project team, ultimately leading to missed deadlines and a subpar project outcome. These setbacks resulted in multiple lost opportunities for the company.

Of course, one could argue that the problem here was caused by my boss inability to manage me. But one can make just as strong an argument that the problem was related to my inability to manage my boss.?

In the dynamic digital travel sector, how do you effectively manage your relationship with your boss on a daily basis? It begins with recognising the mutual dependency between both parties. Identifying key drivers you can integrate into your daily routine will enable you to position yourself favourably, driving mutual benefits for you, your boss, and the company.

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Unlocking Three Key Drivers for Building a Collaborative Relationship with Your Boss

1. Understanding Your Boss

Experiencing a merger within a TravelTech company, where I had multiple bosses in a short period, taught me the importance of being sensitive to each new boss's working style. This enabled me to adapt swiftly to the organisation's evolving needs driven by the merger.

Ask your boss about their preferred working style, and what they do not prefer. For instance, after asking my last boss about her working style, she made it very clear that she is not a morning person. Consequently, I avoided scheduling one-on-one meetings in her morning and ensured that important meetings she needed to attend with me were in the afternoon. By asking, I demonstrated my interest in efficiency and attentiveness as a direct report. This not only made it easier for us to work together but also made it easier for her to connect me with people in her network, exposing me to work that excited me.?

2. Understanding Yourself

Your boss is only one-half of the relationship. You are the other half, as well as the part which you have more direct control. Become aware of any internal obstacles that may hinder or facilitate collaboration with your boss. With this awareness, take proactive actions to enhance the effectiveness of the relationship.

Almost all my bosses have been "big picture" people, inspired by vision. Once, I volunteered to assist a senior leader who worked closely with my boss to establish a partnership alliance with another major global TravelTech company, a venture extending beyond our usual scope.

Facilitating flexibility, I compensated for my boss's busy schedule by attending meetings in her absence. I also worked on tasks during my time zone, while most of the other project leads were asleep, allowing us to establish the desired partnership ahead of schedule.

?Additionally, by providing support and flexibility to the other senior leader which was crucial for promoting my boss's departmental vision, I enabled my boss to achieve more. This collaborative approach demonstrated, rather than just stated, my alignment with my boss’s goals and those around her upon whom she relied. This, in turn, contributed to building a more effective working relationship with my boss.

3. Negotiate with Diplomacy

Negotiating with your boss is an art form that involves persuading someone in authority to see things from your perspective and take action. Therefore, negotiating with diplomacy is crucial.

During my tenue as an organisational leader at Expedia Group , I found those individuals who communicated their ideas diplomatically and emphasised the benefits for both my goals as a department head and the organisation, rather than solely for themselves, were more successful.

During the COVID era, as a department leader, I had a standout team member named Sarah*. She proposed a project aimed at automating our backend airline partnership processes. Instead of presenting it solely as her idea, she framed it in a way that emphasising how it aligned with our department's goals of enhancing airline partnership engagement metrics and Expedia Group 's global objectives of building partnership growth through digital automation She also linked it to the broader Expedia Group global objectives of building partnership growth by establishing better connections through digital automation. By highlighting the mutual benefits and approaching the conversation diplomatically, Sarah gained my full support and secured resources for her project. As a result, her initiative not only succeeded but also significantly contributed to our department's performance, benefiting her career and Expedia Group .

By diplomatically negotiating for your idea and aligning it with reaching your role's goals, benefiting your boss, and contributing to the company's success, you can achieve a win-win-win outcome.

Effective leaders see themselves as ultimately responsible for their achievements within an organisation. They recognise the importance of dedicating time and energy to establish and manage positive relationships with everyone, including their boss. This allows seamless collaboration across departments, clearing the path for travel companies to deliver frictionless travel experiences within the ever-changing digital travel sector.

* To protect confidentiality, the names of team member highlighted in this article have been changed.