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Reintroduced a point which was missed out in the previous edit.
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Masked Man
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Don't impersonate your manager, even if he asks you.

But he has also asked me to use his credentials to take a mandated exam, so that it appears that he was the one taking the exam.

Your company most certainly has a policy against this kind of impersonation, which means both of you would be violating the company policy. Some companies are also known to perform "compliance auditing" by having a person of authority tempt an employee to violate a policy. If your manager is doing this as part of such an audit, then you would fail the audit.

Moreover, your company has ruled that this exam is mandatory, and letting one person take exams on behalf of multiple people reduces that rule to a farce. The company probably has a good reason for making the exam mandatory, so bypassing that can create problems later. For example, the manager could be deputed to work for a client, and they assume that he has a certain level of competency in this subject, as seen from his score in this exam.

How can I tell tell him "No" to that without making him upset or angry.

This is one of the few scenarios where you should not do what the boss asks. However, you should respond with a "positive No" by not only providing a good reason, but also offering alternatives.

Ask him why he cannot take the test, and suggest ways to help him solve that problem. If he finds the material too hard to follow (due to not having the relevant background, for example), offer to teach him or provide self-study material. If he doesn't find the time to study, offer to take up some of his less critical responsibilities for a few days. If you are not senior enough to do that yourself, suggest that he could consider assigning those to a senior team member.

Don't impersonate your manager, even if he asks you.

But he has also asked me to use his credentials to take a mandated exam, so that it appears that he was the one taking the exam.

Your company most certainly has a policy against this kind of impersonation, which means both of you would be violating the company policy. Some companies are also known to perform "compliance auditing" by having a person of authority tempt an employee to violate a policy. If your manager is doing this as part of such an audit, then you would fail the audit.

Moreover, your company has ruled that this exam mandatory, and letting one person take exams on behalf of multiple people reduces that rule to a farce.

How can I tell tell him "No" to that without making him upset or angry.

This is one of the few scenarios where you should not do what the boss asks. However, you should respond with a "positive No" by not only providing a good reason, but also offering alternatives.

Ask him why he cannot take the test, and suggest ways to help him solve that problem. If he finds the material too hard to follow (due to not having the relevant background, for example), offer to teach him or provide self-study material. If he doesn't find the time to study, offer to take up some of his less critical responsibilities for a few days. If you are not senior enough to do that yourself, suggest that he could consider assigning those to a senior team member.

Don't impersonate your manager, even if he asks you.

But he has also asked me to use his credentials to take a mandated exam, so that it appears that he was the one taking the exam.

Your company most certainly has a policy against this kind of impersonation, which means both of you would be violating the company policy. Some companies are also known to perform "compliance auditing" by having a person of authority tempt an employee to violate a policy. If your manager is doing this as part of such an audit, then you would fail the audit.

Moreover, your company has ruled that this exam is mandatory, and letting one person take exams on behalf of multiple people reduces that rule to a farce. The company probably has a good reason for making the exam mandatory, so bypassing that can create problems later. For example, the manager could be deputed to work for a client, and they assume that he has a certain level of competency in this subject, as seen from his score in this exam.

How can I tell tell him "No" to that without making him upset or angry.

This is one of the few scenarios where you should not do what the boss asks. However, you should respond with a "positive No" by not only providing a good reason, but also offering alternatives.

Ask him why he cannot take the test, and suggest ways to help him solve that problem. If he finds the material too hard to follow (due to not having the relevant background, for example), offer to teach him or provide self-study material. If he doesn't find the time to study, offer to take up some of his less critical responsibilities for a few days. If you are not senior enough to do that yourself, suggest that he could consider assigning those to a senior team member.

Made the answer less pessimistic/paranoid, removed anecdote which was just enforcing that pessimism.
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Masked Man
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Don't impersonate your manager, even if he asks you.

But he has also asked me to use his credentials to take a mandated exam, so that it appears that he was the one taking the exam.

AskYour company most certainly has a policy against this kind of impersonation, which means both of you would be violating the company policy. Some companies are also known to perform "compliance auditing" by having a person of authority tempt an employee to violate a policy. If your manager is doing this as part of such an audit, then you would fail the audit.

Moreover, your company has ruled that this exam mandatory, and letting one person take exams on behalf of multiple people reduces that rule to a farce.

How can I tell tell him "No" to that without making him upset or angry.

This is one of the few scenarios where you should whynot do what the boss asks. However, you should respond with a "positive No" by not only providing a good reason, but also offering alternatives.

Ask him why he would prefer youcannot take the test instead of him, and offersuggest ways to help addresshim solve that problem. (Treat the disease, not the symptoms.) If he finds the material too difficulthard to understandfollow (perhaps because he doesn't havedue to not having the relevant background, for example), then offer to teach him or provide him self-study material. If he doesn't find the time to study, offer to temporarily take up some of his less critical responsibilities.

Most companies have a policy against this kind of impersonation, and silly as it might sound, your manager could be doing a "sting operation", as part of for a compliance auditingfew days. If you agree to impersonate him, he has evidence against you!1

Even if this isn't a sting operation, this impersonation isare not only unethical but could also create problems. For instance, suppose your manager is deputedsenior enough to work for a client who requires someone who has completed this certificationdo that yourself, and they find out latersuggest that he did not take this test. When things get ugly (and for your own safety, assume they will), you would get caught up in the mess, and your manager may not cover for you then.


1 Anecdote A company I have worked for was very strict about its tailgating policy (client requirement). Employees would receive frequent admonitions through HR mass mailers, manager's instructions, notice board posters, etc.could consider assigning those to never allow any person, not even youra senior team member or manager, to enter the restricted areas without a valid ID badge.

Managers would sometimes pretend to have forgotten their ID badge (or a similar excuse) and plead with an employee to let them tailgate "since you know I work here anyway". Employees who directed them to the access control office "passed" the test, while those who complied with the request would be reprimanded by the same manager.

Don't impersonate your manager, even if he asks you.

Ask your manager why he would prefer you take the test instead of him, and offer to help address that problem. (Treat the disease, not the symptoms.) If he finds the material too difficult to understand (perhaps because he doesn't have the relevant background), then offer to teach him or provide him self-study material. If he doesn't find the time to study, offer to temporarily take up some of his less critical responsibilities.

Most companies have a policy against this kind of impersonation, and silly as it might sound, your manager could be doing a "sting operation", as part of a compliance auditing. If you agree to impersonate him, he has evidence against you!1

Even if this isn't a sting operation, this impersonation is not only unethical but could also create problems. For instance, suppose your manager is deputed to work for a client who requires someone who has completed this certification, and they find out later that he did not take this test. When things get ugly (and for your own safety, assume they will), you would get caught up in the mess, and your manager may not cover for you then.


1 Anecdote A company I have worked for was very strict about its tailgating policy (client requirement). Employees would receive frequent admonitions through HR mass mailers, manager's instructions, notice board posters, etc. to never allow any person, not even your team member or manager, to enter the restricted areas without a valid ID badge.

Managers would sometimes pretend to have forgotten their ID badge (or a similar excuse) and plead with an employee to let them tailgate "since you know I work here anyway". Employees who directed them to the access control office "passed" the test, while those who complied with the request would be reprimanded by the same manager.

Don't impersonate your manager, even if he asks you.

But he has also asked me to use his credentials to take a mandated exam, so that it appears that he was the one taking the exam.

Your company most certainly has a policy against this kind of impersonation, which means both of you would be violating the company policy. Some companies are also known to perform "compliance auditing" by having a person of authority tempt an employee to violate a policy. If your manager is doing this as part of such an audit, then you would fail the audit.

Moreover, your company has ruled that this exam mandatory, and letting one person take exams on behalf of multiple people reduces that rule to a farce.

How can I tell tell him "No" to that without making him upset or angry.

This is one of the few scenarios where you should not do what the boss asks. However, you should respond with a "positive No" by not only providing a good reason, but also offering alternatives.

Ask him why he cannot take the test, and suggest ways to help him solve that problem. If he finds the material too hard to follow (due to not having the relevant background, for example), offer to teach him or provide self-study material. If he doesn't find the time to study, offer to take up some of his less critical responsibilities for a few days. If you are not senior enough to do that yourself, suggest that he could consider assigning those to a senior team member.

Wrong emphasis, fixed now.
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Masked Man
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Don't impersonate your manager, even if he asks you.

Ask your manager why he would prefer you take the test instead of him, and offer to help address that problemthat problem. (Treat the disease, not the symptoms.) If he finds the material too difficult to understand (perhaps because he doesn't have the relevant background), then offer to teach him or provide him self-study material. If he doesn't find the time to study, offer to temporarily take up some of his less critical responsibilities.

Most companies have a policy against this kind of impersonation, and silly as it might sound, your manager could be doing a "sting operation", as part of a compliance auditing. If you agree to impersonate him, he has evidence against you!1

Even if this isn't a sting operation, this impersonation is not only unethical but could also create problems. For instance, suppose your manager is deputed to work for a client who requires someone who has completed this certification, and they find out later that he did not take this test. When things get ugly (and for your own safety, assume they will), you would get caught up in the mess, and your manager may not cover for you then.


1 Anecdote A company I have worked for was very strict about its tailgating policy (client requirement). Employees would receive frequent admonitions through HR mass mailers, manager's instructions, notice board posters, etc. to never allow any person, not even your team member or manager, to enter the restricted areas without a valid ID badge.

Managers would sometimes pretend to have forgotten their ID badge (or a similar excuse) and plead with an employee to let them tailgate "since you know I work here anyway". Employees who directed them to the access control office "passed" the test, while those who complied with the request would be reprimanded by the same manager.

Don't impersonate your manager, even if he asks you.

Ask your manager why he would prefer you take the test instead of him, and offer to help address that problem. (Treat the disease, not the symptoms.) If he finds the material too difficult to understand (perhaps because he doesn't have the relevant background), then offer to teach him or provide him self-study material. If he doesn't find the time to study, offer to temporarily take up some of his less critical responsibilities.

Most companies have a policy against this kind of impersonation, and silly as it might sound, your manager could be doing a "sting operation", as part of a compliance auditing. If you agree to impersonate him, he has evidence against you!1

Even if this isn't a sting operation, this impersonation is not only unethical but could also create problems. For instance, suppose your manager is deputed to work for a client who requires someone who has completed this certification, and they find out later that he did not take this test. When things get ugly (and for your own safety, assume they will), you would get caught up in the mess, and your manager may not cover for you then.


1 Anecdote A company I have worked for was very strict about its tailgating policy (client requirement). Employees would receive frequent admonitions through HR mass mailers, manager's instructions, notice board posters, etc. to never allow any person, not even your team member or manager, to enter the restricted areas without a valid ID badge.

Managers would sometimes pretend to have forgotten their ID badge (or a similar excuse) and plead with an employee to let them tailgate "since you know I work here anyway". Employees who directed them to the access control office "passed" the test, while those who complied with the request would be reprimanded by the same manager.

Don't impersonate your manager, even if he asks you.

Ask your manager why he would prefer you take the test instead of him, and offer to help address that problem. (Treat the disease, not the symptoms.) If he finds the material too difficult to understand (perhaps because he doesn't have the relevant background), then offer to teach him or provide him self-study material. If he doesn't find the time to study, offer to temporarily take up some of his less critical responsibilities.

Most companies have a policy against this kind of impersonation, and silly as it might sound, your manager could be doing a "sting operation", as part of a compliance auditing. If you agree to impersonate him, he has evidence against you!1

Even if this isn't a sting operation, this impersonation is not only unethical but could also create problems. For instance, suppose your manager is deputed to work for a client who requires someone who has completed this certification, and they find out later that he did not take this test. When things get ugly (and for your own safety, assume they will), you would get caught up in the mess, and your manager may not cover for you then.


1 Anecdote A company I have worked for was very strict about its tailgating policy (client requirement). Employees would receive frequent admonitions through HR mass mailers, manager's instructions, notice board posters, etc. to never allow any person, not even your team member or manager, to enter the restricted areas without a valid ID badge.

Managers would sometimes pretend to have forgotten their ID badge (or a similar excuse) and plead with an employee to let them tailgate "since you know I work here anyway". Employees who directed them to the access control office "passed" the test, while those who complied with the request would be reprimanded by the same manager.

Added anecdote in support of the "sting operation" claim.
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Masked Man
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Masked Man
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