askST Jobs: How do I deal with multiple bosses at once?

Manpower reporter Tay Hong Yi offers practical answers to candid questions on navigating workplace challenges and getting ahead in your career. Get more tips by signing up to The Straits Times’ HeadSTart newsletter.

Q: I report to multiple leaders at work. How do I effectively balance what they each want from me?

A: It is becoming increasingly typical for employees to report to more than one boss, says Dr David Leong, managing director of PeopleWorldwide Consulting.

Those in larger multi-nationals may even have to report to different bosses across geographical boundaries, he adds.

Organisations may opt for a reporting structure with multiple leaders to encourage collaboration across functional lines, tap a wide range of skills and guarantee that projects benefit from a variety of views.

“When it comes to handling difficult issues, this configuration has the potential to result in more creative ideas and a more comprehensive approach,” says Dr Leong.

Mr Linus Choo, regional executive director of executive search firm Ethos BeathChapman, also notes that employees, especially promising talents, may be expected to liaise with multiple stakeholders due to projects or assignments that straddle different business functions or regions.

“In such a system, it is probably more efficient to have the individual report to multiple leaders, though ideally not more than three to be efficient, as a key project manager who is the subject-matter expert.”

Such a set-up enables quicker decision-making, especially in dynamic situations, Mr Choo notes, adding: “Employees are able to see the bigger picture instead of operating in silos.”

Someone placed in this situation needs to be comfortable with each boss having different expectations, communication styles and timelines, which need to be prioritised, he says.

Dr Leong notes that such workers must be comfortable with ambiguity, as they may be dealing with conflicting instructions and orders from different bosses with overlapping deadlines.

“In order to properly coordinate work, you will need to be able to handle competing priorities and have a solid understanding of the strategic requirements of each leader,” he says, a process that entails clear communication that establishes expectations.

“Please keep each leader up to date on your progress and workload on a regular basis.”

Meanwhile, leaders should work together to coordinate their calls for action and deliver consistent feedback, Dr Leong advises.

“Regular check-ins, online or face-to-face, are beneficial for both talents and bosses since they ensure alignment and allow for the resolution of any issues or overlaps in expectations that may arise.”

For their part, talents should prioritise jobs according to their level of significance and urgency, and convey their ability in an open and honest manner.

Dr Leong notes: “When you are talking about your workload, you should frame it in terms of how it affects the quality and timeliness of your production, raising conflicts of interests or overlapped deadlines so that they can be resolutely resolved (in a way) that would not compromise work output.

“This will prevent you from giving the impression that you are avoiding an obligation, or fail to deliver because of a compressed timeline.”

For instance, he suggests that employees may candidly state their current workload and timeline, framing it as an effort to determine whether they will be able to give this project the attention it requires.

While it is a possibility that this reporting arrangement is a cost-cutting measure by pushing someone to cover work that should be spread across multiple others, Mr Choo says this is more likely meant to groom promising talent.

“As you interact with more stakeholders on a daily basis, it offers you a chance to implement change across different business units, and also allows stakeholders to provide you with endorsements, which is important since you probably require visibility during promotion cycles in multi-nationals,” he adds.

Mr Choo also says that as long as the scope of work is defined well, someone should know the work that is not essential or pressing.

“In that instance, if you are a talent put in that position, you should learn to speak up, push back or put out a holding response to buy you some time to work on non-prioritised tasks.”

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